Tag: M.W=200-300

Synthetic Route of 112101-81-2,Some common heterocyclic compound, 112101-81-2, name is R-5-(2-Aminopropyl)-2-methoxybenzenesulfonamide, molecular formula is C10H16N2O3S, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

Into a 4-necked 500ml round bottom flask, equipped with Dean-stark apparatus 150.0ml of toluene, 24.4gms of (R)-5-(2-aminopropyl)-2-methoxy benzene sulfonamide of the formula-IV and 12.4gms (0.1mole) of 4-fluorobenzaldehyde are charged. The reaction is effected azeotropically and the water 1.8ml (0.1mole) is separated. Then the toluene is distilled off completely under vacuum at temp max 80C. Cooled 25-35C and released the vacuum under nitrogen atmosphere – 25.0gm of thick oily compound of 2-methoxy-5-(2R)-2-{[(1-E/Z-4-fluorophenylpmethylene)amino] propyl} benzenesulfonamide of formula-IIId is obtained. Recrystallized sample (from IPA) has the following characteristics MR : 140-148C 1H NMR : (200MHz, CDCl3+DMSO-d6) delta 1.01-1.04 (d, 3H), 2.80-2.88 (t, 2H), 3.14 – 3.18 (m, 1H), 3.88 (s, 3H), 6.0, (broad, 2H), 7.12-7.57 (aromatic, 7H), 8.20 (s, imine, 1H) IR : (KBr), 3385, 3315, 2948, 1643, 1606, 1576, 1495, 1404, 1334, 1249, 1154, 1074, 1114, 518, 471cm-1

The synthetic route of 112101-81-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NATCO PHARMA LIMITED; WO2004/16582; (2004); A1;,
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Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 3460-23-9, name is N-(4-Bromo-2-chlorophenyl)acetamide, This compound has unique chemical properties. The synthetic route is as follows., Safety of N-(4-Bromo-2-chlorophenyl)acetamide

Compound alpha (1 g, 4.8 mmol) was dissolved in 10 mL of anhydrous methylene chloride. To this mixture was added triethylamine (0.68 mL, 4.8 mmol) and the reaction was stirred at room temperature for 5 min. Acetyl chloride (0.5 mL, 7.2 mmol) was then added at 0 0C and the mixture stirred at room temperature for 2 hours. Water and dichloromethane were added and the layers separated. The organic layer was then dried over sodium sulfate and concentrated to give 1.11 g, 92% yield of compound b. To a solution of b (500 mg, 2.01 mmol), cyclopropyl boronic acid (225 mg, 2.62 mmol), potassium phosphate (1.49 g, 7.04 mmol) and tricyclohexylphosphine (56 mg, 0.2 mmol) in toluene (10 mL) and water (0.4 mL) under nitrogen atmosphere was added palladium acetate (23 mg, 0.1 mmol). T he mixture was heated to 100 0C for 3h and then cooled to room temperature. Water was added and the mixture extracted with ethyl acetate, dried over sodium sulfate and concentrated to give 550mg of crude product c that was used in the next step without further purification. Compound c (500mg, 2.4 mmol) was dissolved in 4 mL of ethanol. Aqueous IN HCl (4 mL) was added and the mixture stirred at reflux for 8 hours. The solvent was removed in vacuo to afford 440mg of compound d which was used in the next step without further purification. Compound d (440mg, 2.6 mmol) was dissolved in 14 mL of dichloromethane. Sodium bicarbonate (7 mL, sat. solution) and thiophosgene (0.2 mL, 2.6 mmol) were added and the mixture stirred at room temperature for Ih. Then, the organic layer was separated, dried over sodium sulfate and concentrated to afford 877 mg, 99% yield of compound e which was used in the next step without further purification Compound e (447mg, 2.1 mmol) was dissolved in 3 mL of dimethylformamide, aminoguanidine hydrochloride salt (355 mg, 3.2 mmol) and diisopropyl ethylamine (0.56 mL, 3.2 mmol) were added and the mixture stirred at 50 0C for 18 hours. The mixture was then concentrated and to the resulting residue was added 2M aqueous sodium hydroxide solution (10 mL). The mixture was stirred at 50 0C for 18 hours and then cooled to room temperature. The resulting mixture was then neutralized with aqueous IN HCl and the precipitate (product) collected to give compound/ (240 mg, 44% yield) Compounds/(89mg, 0.33 mmol) and g (94mg, 0.33 mmol) were dissolved in DMF (1.5 mL) and potassium carbonate (51mg, 0.37 mmol) was added. The mixture was stirred at room temperature for 18 hours. Water was then added to the mixture and the precipitate formed collected and purified by prep. TLC (90% dichloromethane/ 10% methanol) to give 116 mg, 68% yield of compound h. Dichloroacetic acid (0.04 mL, 0.46 mmol) was added to a mixture of compound h (116mg, 0.23 mmol), benzyltriethyl ammonium bromide (183mg, 0.68 mmol) and sodium nitrite (304mg, 4.6 mmol) in dibromomethane (5 mL). The mixture was stirred at room temperature for 18 hours in the dark. The reaction mixture was then concentrated and the resulting residue was purified by prep. TLC (95% dichloromethane /5% methanol) to afford 99.10 mg of the sulfonic acid and 17.90 mg of title compound i.

According to the analysis of related databases, 3460-23-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; VALEANT RESEARCH & DEVELOPMENT; WO2006/26356; (2006); A2;,
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Electric Literature of 174799-52-1, A common heterocyclic compound, 174799-52-1, name is tert-Butyl (2-(benzylamino)ethyl)carbamate, molecular formula is C14H22N2O2, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

41 c (5.00g, 17.96 mmol) and 56 (4.497g, 17.96 mmol, 1 eq) were dissolved in EtOH (30 mL) and a few drops of water added, before splitting the mixture into 2 x 30 mL W vessels. Each mixture was heated at 100 C for 30 mins in the MW reactor (dynamic program with maximum pressure 250 psi, maximum power 300W). Concentration of the reaction mixture gave approximately 10 g of crude residue. This was purified by FCC (eluent PE/DCM 1 :1 to prime/load the column, with the gradient increasing to 100% DCM over 5CV, 1 00% DCM for a further 3 CV and then raise to DCM/MeOH 99:1 over 1 CV, then to 95:5 over 3 CV, holding at this concentration to elute the desired product). This gave 7.30 (77%) g of white crystalline solid.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; THE UNIVERSITY OF NOTTINGHAM; MISTRY, Shailesh; DARAS, Etienne; FROMONT, Christophe; JADHAV, Gopal; FISCHER, Peter Martin; KELLAM, Barrie; HILL, Stephen John; BAKER, Jillian Glenda; WO2012/4549; (2012); A1;,
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Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 2618-96-4, name is Dibenzenesulfonimide, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: Dibenzenesulfonimide

General procedure: To a solution of N-sulfonylsulfonamide 1 (1.68 mmol) in N,N-disubstituted formamide 3 (3.0 mL) was added TsCl (2; 0.160 g, 0.840 mmol; 0.480 g, 2.52 mmol for products 4d-g) and Et3N (0.29 mL, 2.10 mmol). The mixture was stirred at r.t. (or heated to 100 C in the cases of 4d-g,k). After the starting material was consumed as indicated by TLC, the reaction mixture was poured into H2O and extracted with CH2Cl2. The combined organic phases were washed with H2O, dried (anhydrous MgSO4), filtered, and concentrated under reduced pressure. The crude product was purified, if necessary, by silica gel flash column chromatography (hexane/EtOAc) to give the desired product as a white solid (Table 2).

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 2618-96-4.

Reference:
Article; Jeong, Yuri; Ban, Jaeyoung; Lim, Minkyung; Rhee, Hakjune; Synthesis; vol. 50; 9; (2018); p. 1867 – 1874;,
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Application of 621-38-5, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 621-38-5, name is 3-Bromoacetanilide belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Methyllithium (1.4 M in diethyl ether, 37.4 ml, 52.3 mmol) was added to a -78 C. solution of 3-bromoacetanilide (11.5 g, 53.7 mmol) in tetrahydrofuran (250 ml). The reaction was stirred 15 min at -78 C. Tert-butyllithium (1.7 M in pentane, 62.4 ml, 106 mmol) was added over 30 min to the -78 C. reaction mixture. The reaction was stirred 10 min at -78 C. N-methoxy-N-methyl (1-methyl(4-piperidyl))formamide (5.0 g, 26.8 mmol) in tetrahydrofuran (20 ml) was added dropwise to give a homogeneous yellow solution. The reaction mixture was stirred and allowed to warm to room temperature over 21 hours. The reaction mixture was cooled to 10 C., quenched with ice, and extracted with 1N hydrochloric acid solution. The aqueous extracts were washed with diethyl ether, basified to pH 12 with 5N sodium hydroxide solution and extracted with diethyl ether. The diethyl ether extracts were dried over sodium sulfate and the solvent was removed under reduced pressure to give 6.1 g of a yellow oil. The basic aqueous solution was again extracted with chloroform/isopropanol (3:1). These extracts were dried over sodium sulfate and the solvent was removed under reduced pressure to give 3.4 g of a yellow oil. Both oils were combined and purified by flash chromatography (silica gel, methylene chloride:methanol:ammonium hydroxide, 100:7.5:0.75) to yield 5.7 g (81%) of product as a yellow oil. [00418] MS(m/e): 261(M+1), 259(M-1).

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 3-Bromoacetanilide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Eli Lilly and Company; US6777428; (2004); B1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Some common heterocyclic compound, 209917-48-6, name is N-tert-Butyl 4-Aminophenylsulfonamide, molecular formula is C10H16N2O2S, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. SDS of cas: 209917-48-6

Step 3; To a mixture of 4-amino-N-tert-butylbenzenesulfonamide (180 mg, 0.788 mmol, from step 2) and 3,3-dimethyl-2-oxobutanoic acid (308 mg, 2.4 mmol) in a 100 ml RBF at RT was added tetraisopropoxytitanium (2 ml,) via a pipet. The color of the mixture soon changed into a characteristic canary color. The solution was warmed to 75 C. for about 15 minutes and the color remained the same. The solution was diluted with absolute ethanol (8 ml) at RT, followed by the addition of 1.5× of sodium cyanotrihydroborate (245 mg, 3.90 mmol), and the remaining half after the bubbling and sizzling was over. The color of the solution became lighter. The solution was mixed with 4 mL of water, forming a suspension, and the white PPT was removed by centrifuge. The organic was extracted into ethyl acetate, and the organic phase was dried over Na2SO4, filtered, and evaporated to dryness. A yellow oil was obtained and was used directly in the next step without further purification. LC-MS, MS m/z 343 (M++H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 209917-48-6, its application will become more common.

Reference:
Patent; Bristol-Myers Squibb Company; US2008/119461; (2008); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Some common heterocyclic compound, 688790-06-9, name is 7-tert-Butyl 2-methyl 7-azabicyclo[2.2.1]heptane-2,7-dicarboxylate, molecular formula is C13H21NO4, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. Product Details of 688790-06-9

A solution of 4M HCl in dioxane (100 mL, 400 mmol, 3.0 eq) was slowly added to a stirred solution of 7-tert-butyl 2-ethyl 3-bromo-7-azabicyclo[2.2.1]heptane-2,7-dicarboxylate (20.0 g, 74.3 mmol, 1.0 eq) in dioxane (400 mL) at 0 C and the reaction mixture was stirred at room temperature for 2 h. After completion of the reaction (monitored by TLC, 30% ethyl acetate-hexane, R = 0.01), solvent was removed under reduced pressure and the residue was dried under vacuum to afford ethyl 7-azabicyclo[2.2.1]heptane-2-carboxylate HC1 (12.0 g, 96%) as a yellow sticky mass. LCMS m/z = 156.12 (M+l); crude purity by 1H NMR -90%. [

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 688790-06-9, its application will become more common.

Reference:
Patent; INNOV 17 LLC; TILLEY, Jefferson; BLINN, James; GAWECO, Anderson; (93 pag.)WO2016/14918; (2016); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

68524-30-1,Some common heterocyclic compound, 68524-30-1, name is 2-[(Diphenylmethyl)thio]acetamide, molecular formula is C15H15NOS, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

EXAMPLE 1; [0289 ] In this Example, the modafinil intermediate compound benzhydrylthioacetamide was oxidized to produce modafinil according to the processes described herein using various ratios of alcohol to organic acid and various reaction mixture temperatures.[0290] First, benzhydrylthioacetamide (10 g; MW = 257.35; 1.0 eq.), methanol, and acetic acid were charged to a 250 ml_ flask. Hydrogen peroxide (4.3 ml 1.05 eq.) was then charged to the resulting mixture over the course of about 5 minutes. The reaction was allowed to proceed for about 24 hours, with samples periodically taken for HLPC analysis. Several different trials using particular ratios of methanol and acetic acid at particular temperatures were performed. Results are illustrated in Tables 1-7, below.Table 1 : 20 ml_ methanol/20 mL acetic acid; 400CTable 2: 30 mL metha?ol/10 mL acetic acid; 400CTable 3: 35 mL methanol/5 mL acetic acid; 400C Table 4: 39 mL methanol/1 mL acetic acid; 400C [0291] As illustrated in Tables 1-7 above, the processes of the present invention are effective in producing modafinil at high yield and with relatively low sulfone impurity content. Specifically, as illustrated in Table 2, a reaction mixture comprising 30 mL of methanol and 10 mL acetic acid (i.e., methanol and acetic acid are present in the reaction mixture at a ratio of about 3:1 ) with the oxidation reaction proceeding at 400C is particularly effective, producing modafinil at about 96% yield with a sulfone impurity content of about 0.22%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-[(Diphenylmethyl)thio]acetamide, its application will become more common.

Reference:
Patent; MALLINCKRODT INC.; WO2007/70238; (2007); A2;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 16313-66-9, name is 2-Amino-5-bromobenzamide, belongs to amides-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 16313-66-9, name: 2-Amino-5-bromobenzamide

To a solution of compound 5-4-2 (22.0 g, crude product) in dry THF (250 mL), compound 1-19 (7.6 g, 35.5 mmol) and NaOH (1 M, 85.0 mmol) were added in turn. At the end of the addition, the mixture was stirred at rt for 1.0 hr. After the reaction was completed, the mixture was extracted with EtOAc (100 mL x 3). The combined organic layers were washed with NaOH aqueous solution (1 M.15 mL) and brine, dried over Na2S04and concentrated in vacuo to give the title compound (17.0 g, 100%). The compound was characterized by the following spectroscopic data:MS (ESI, pos.ion) mlz: 446.5 [M+H]’; and NMR (400 MHz. CDCL) delta (ppm): 9.06 (br, 1H), 7.75 (d, 1H).7.35.7.33 (d. d.1 H).7.28-7.22 (m, 5H). 6.69.6.67 (d. d.1H), 5.68 (brs.2H).5.14-5.13 (m, 2H).4.29-4.25 (m.1H), 3.66-3.60 (m, 1H), 3.45-3.37 (m. 1H), 2.39-2.32 (m.1H), 2.09-2.00 (m.1H), 1.96-1.77 (m, 2H).

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; SUNSHINE LAKE PHARMA CO.,LTD.; ZHANG, Jiancun; ZHANG, Yingjun; XIE, Hongming; REN, Qingyun; HU, Bailin; FU, Changping; WU, Xiwei; LI, Shifeng; WANG, Chenglin; ZHANG, Zhikeng; WO2014/82379; (2014); A1;,
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Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 87905-98-4, name is Benzyl (5-hydroxypentyl)carbamate, A new synthetic method of this compound is introduced below., category: amides-buliding-blocks

Benzoyl chloride (0.88 mL, 7.59 mmol) was added dropwise to a stirred solution of benzyl (5-hydroxypentyl) carbamate (commercially available) (1.5 g, 6.32 mmol) in anhydrous CH2C12 (15 mL) containing Et3N (1.76 mL, 1.26 mmol) at 0 C. After 1 minute DMAP (1.7 g, 13.9 mmol) in anhydrous CH2CI2 (10 mL) was added dropwise to the reaction mixture and stirred at rt overnight. The resulting mixture was diluted with CH2CI2 (-30 mL) and washed with aq. HC1 (1M, 1 x 10 mL), water (60 mL), sat. aq. NaHC03 (30 mL), and brine (30 mL). The organic phase was separated, dried over MgS04, and concentrated in vacuo. The residue was quickly filtered off on silica gel (ethyl acetate – hexane gradient elution) to afford the almost pure compound as oil. This crude material was directly used for benzylation. To the solution of benzoyl protected compound (0.9 g, 2.63 mmol) dissolved in anhydrous DMF (10 mL) was added NaH (0.12 g, 2.89 mmol) at 0 C. The mixture was stirred at 0 C for 45 min, and then BnBr (0.37 mL, 3.16 mmol) were added. After stirring for another 12 h when TLC showed that the reaction was completed, it was quenched with H20 at 0 C, and the mixture was diluted with EtOAc. The aqueous layer was extracted with EtOAc (5 chi 25 mL), and the organic phases were combined and dried over Na2S04. The desired product S13 (1.093 g, 96.1%) was obtained upon flash column chromatography (ethyl acetate – hexane gradient elution) of the condensed product.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; THE SECRETARY OF STATE FOR ENVIRONMENT, FOOD AND RURAL AFFAIRS; THE GOVERNORS OF THE UNIVERSITY OF ALBERTA; MCGIVEN, John; HOWELLS, Laurence; DUNCOMBE, Lucy; BUNDLE, David; MANDAL, Satadru Sekhar; SARKAR, Susmita; (101 pag.)WO2018/83490; (2018); A2;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics