Tag: M.W=200-300

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. 6162-21-6, name is 4-(Dimethylamino)benzenesulfonamide, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of 4-(Dimethylamino)benzenesulfonamide

General procedure: A suspension of potassium hydride (3 equiv) in THF (0.6 M) was cooled in an ice-water bath. A solution of sulfonamide, sulfonamide or aniline (1.0 equiv) in THF (0.20 M) was added dropwise, and the suspension was stirred for 15 min. 1,1′-Carbonyldiimidazole (1.0 equiv) was dissolved in 1:1 THF/dioxane (0.20 M) and added dropwise to the reaction mixture, resulting in the formation of a white precipitate. The ice-water bath was removed, and the reaction mixture was allowed to warm to ambient temperature and was stirred for 2 h. A solution of diamine S-1 (1.0 equiv) in THF (1.0 M) was added dropwise, and the suspension was stirred at room temperature for 20 h. The reaction was quenched with a solution of acetic acid (3 equiv) in THF (1.0 M). The crude product was concentrated in vacuo and purified by silica gel chromatography.

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 6162-21-6.

Reference:
Article; Kimmel, Kyle L.; Robak, Maryann T.; Thomas, Stephen; Lee, Melissa; Ellman, Jonathan A.; Tetrahedron; vol. 68; 12; (2012); p. 2704 – 2712;,
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Electric Literature of 16313-66-9,Some common heterocyclic compound, 16313-66-9, name is 2-Amino-5-bromobenzamide, molecular formula is C7H7BrN2O, 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.

General procedure: 3.3.1 6-Bromo-8-iodo-2-phenylquinazolin-4(3H)-one (4a) A stirred mixture of 2 (1.00 g, 2.94 mmol), benzaldehyde (0.37 g, 3.52 mmol) and iodine (1.49 g, 5.88 mmol) in ethanol (100 mL) was refluxed for 7 h and then allowed to cool to room temperature. The mixture was quenched with an ice-cold aqueous sodium thiosulfate solution and the precipitate was filtered and recrystallized to afford 4a as a white solid. 6-Bromo-2-(4-chlorophenyl)-8-iodoquinazolin-4(3H)-one (4c). A stirred mixture of 2 (1.00 g, 2.95 mmol), 4-chlorobenzaldehyde (0.49 g, 3.54 mmol) and iodine (1.49 g, 5.90 mmol) in ethanol (100 mL) afforded 4c as a white solid (1.24 g, 91%), mp. > 345 C; numax (ATR) 490, 526, 554, 686, 729, 791, 944, 1014, 1095, 1285, 1428, 1467, 1559, 1602, 1662, 3072, 3159 cm-1; deltaH (500 MHz, DMSO-d6) 7.66 (d, J = 9.0 Hz, 2H), 8.19 (d, J = 2.0 Hz, 1H), 8.28 (d, J = 9.0 Hz, 2H), 8.49 (d, J = 2.0 Hz, 1H), 12.91 (br s, 1H); deltaC (125 MHz, DMSO-d6) 103.4, 122.9, 128.3, 128.8, 128.9, 129.3, 130.2, 137.4, 144.3, 146.0, 147.9, 161.6; m/z 461 (100, MH+); HRMS (ES): MH+, found 460.8550. C14H879Br 35ClIN2O+ requires 460.8553.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Amino-5-bromobenzamide, its application will become more common.

Reference:
Article; Paumo, Hugues K.; Mphahlele, Malose J.; Rhyman, Lydia; Ramasami, Ponnadurai; Tetrahedron; vol. 72; 1; (2016); p. 123 – 133;,
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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. 456-64-4, name is 1,1,1-Trifluoro-N-phenylmethanesulfonamide, A new synthetic method of this compound is introduced below., Product Details of 456-64-4

Example 4 Preparation of; A solution of N-phenyltrifluoromethanesulfonamide (0.97 g) and N,N-diisopropylethylamine (0.58 g) in dry THF (3.9 g) was added to a stirred solution of the product of Preparative Example 3 (1.0 g) in dry THF (4.0 g) within a round bottom flask. This mixture was allowed to stir overnight. The volatile components were then removed using a rotary evaporator. The residue was dissolved in chloroform (40 mL) and was washed first with 0.1N aqueous HCl (40 mL) and then with saturated aqueous sodium chloride. The organic phase was dried over magnesium sulfate and was then filtered. The volatile components were removed using a rotary evaporator to afford 1.03 g of 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; 3M Innovative Properties Company; US2005/107615; (2005); A1;,
Amide – Wikipedia,
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In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 25625-57-4 as follows. Quality Control of 2-Bromo-N-(3-(trifluoromethyl)phenyl)acetamide

Example 5: 2-[3-(4-Bromophenyl)-2-oxo-7-oxa-1 ,4-diazaspiro[4.5]dec-3-en-1 -yl]-N-[3- (trifluoromethyl)phenyl]acetamide; 3-(4-Bromophenyl)-7-oxa-1 ,4-diazaspiro[4.5]dec-3-en-2-one (D19) (100mg, 0.32mmol) in DMF (4ml) was cooled to ice bath temp and treated with sodium hydride (14.23 mg, 0.356 mmol) under an atmosphere of argon. The mixture was stirred for 30 minutes then 2- bromo-N-[3-(trifluoromethyl)phenyl]acetamide (D16) (100 mg, 0.356 mmol) in DMF (2ml) was added over 1.5 hour by syringe pump. The mixture was then allowed to warm to room temp overnight. The mixture was poured into water and extracted with ethyl acetate. The ethyl acetate layer was washed with brine and dried using sodium sulphate and the solvent was removed. The residue was chromatographed on a silica column eluted with a gradient of 0-5% methanol in DCM. A mixture was obtained which was purified by low pH MDAP to give the title compound (81 mg).1H NMR (d6DMSO) delta: 1.65-1.80 (2H, m), 2.06-2.28 (2H, m), 3.5 (1 H, m), 3.65 (1 H, m), 3.8-3.95 (2H, m), 4.5 (2H, m), 7.42 (1 H, m), 7.61 (1 H, m), 7.77 (3H, m) 8.08 (1 H, m), 8.32 (2H, s), 10.6 (1 H, s). 19F NMR (DMSO) delta: -61.4 (s), Mass Spectrum (Electrospray LC/MS): Found 510 (MH+). Ret. time 3.33 min.

According to the analysis of related databases, 25625-57-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GLAXO GROUP LIMITED; UNIVERSITY OF NOTTINGHAM; WO2008/92877; (2008); A2;,
Amide – Wikipedia,
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Some common heterocyclic compound, 127-77-5, name is 4-Amino-N-phenylbenzenesulfonamide, molecular formula is C12H12N2O2S, 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. HPLC of Formula: C12H12N2O2S

To a well-stirred solution of compound 2 (2.48 g, 0.01 mol) inchloroform, benzoyl chloride (1.28 ml, 0.011 mol) in chloroformwas added dropwise at 0 C and stirring was continued in cold condition.After the completion of reaction (monitored by TLC), thereaction mixture was poured into ice cold water. White solid wasfiltered, washed with acetic acid and sodium bicarbonate solutions,dried and purified by recrystallization. Single crystals suitable fordiffraction studies were obtained by slow evaporation fromethanol.Analytical and physical data: Formula: C19H16N2O3S; Yield:70-75%; LCMS (+ve mode): (M + H) = 353.0 (99.5%), RT – 4.349;HRMS: Obtained m/z = 375.0777 (M + Na), cald. = 375.0779.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 127-77-5, its application will become more common.

Reference:
Article; Lahtinen, Manu; Kudva, Jyothi; Hegde, Poornima; Bhat, Krishna; Kolehmainen, Erkki; Nonappa; Venkatesh; Naral, Damodara; Journal of Molecular Structure; vol. 1060; 1; (2014); p. 280 – 290;,
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Synthetic Route of 2618-96-4, The chemical industry reduces the impact on the environment during synthesis 2618-96-4, name is Dibenzenesulfonimide, I believe this compound will play a more active role in future production and life.

Iodobenzene diacetate(579.8 mg, 1.8 mmol)And bis (benzenesulfonyl) imide(535.23 mg, 1.8 mmol) was added toIn acetonitrile,The mixture was stirred at 40 C. for 30 minutes.After that, N-pivaleindole (301.9 mg, 1.5 mmol) was added toAnd the mixture was stirred at room temperature for 3 hours.After removal of the solvent, ether was added,Filter,Washed with ethyl acetate,1- (2,2-Dimethyl-1-oxopropyl)-3- [bis(Benzenesulfone)Amidyl](Phenyl)-lambda 3 -iodanyl]-1 H-indole(893.28 mg, 85%).

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, Dibenzenesulfonimide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Chiba University; Moriyama, Katsuhiko; Togo, Hideo; Ishida, Kazuma; (40 pag.)JP2015/34144; (2015); A;,
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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. Safety of 7-tert-Butyl 2-methyl 7-azabicyclo[2.2.1]heptane-2,7-dicarboxylate

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,
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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., Product Details of 87905-98-4

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

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, Recommanded Product: 16313-66-9

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;,
Amide – Wikipedia,
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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. Product Details of 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