Tag: M.W=100-200

Synthetic Route of 37073-15-7, The chemical industry reduces the impact on the environment during synthesis 37073-15-7, name is 1-(Methylsulfonyl)-1H-benzo[d][1,2,3]triazole, I believe this compound will play a more active role in future production and life.

A flame-dried, two necked, round bottomed flask was charged with methanesulfonyl benzotriazole (34b) (1.0 g, 0.005 mol), 2-furoic acid (0.57 g, 0.005 mol), dry triethylamine (2 ml_), and dry THF (20 ml_) under argon. The resulting solution was heated at reflux for 18 hours. After this time, the THF was removed under reduced pressure to afford a cream coloured residue, which was taken up in ethyl acetate and washed with 1 M HCI (3 chi 30 ml_). The ethyl acetate was dried (MgS04) and removed in vacuo to afford a white solid which was recrystallised from toluene to give the title compound (34c) as fluffy white crystals (0.82 g, 77.0 %); mp 171 – 172 C; Rf = 0.48 (DCM : petroleum ether, 5 : 5); Analysis Calcd. for Cn H7N302: C, 61.97; H, 3.31 ; N, 19.71 %. Found C, 61.73; H, 3.31 ; N, 19.71 %; vmax (KBr) / cm”1 3142 (NH), 1681 (C=0), 1556, 1447; deltaEta (d6-DMSO, 300 MHz) 8.30 (3H, m, H5, H8, H5), 8.08 (1 H, dd, 3. 4.= 3.8, Jy, v= 0.6, H3), 7.82 (1 H, td, J6, 5/ 7= 7.2, 6, 8= 1.2, H6), 7.65 (1 H, td, J7, 6/s=7.2, J7, 5= 1.2, H7), 6.94 (1 H, dd, 4. 3.= 3.8, 4. 5.= 1.8, H4); 5c(d6-DMSO, 75 MHz) 155.0 (CO), 150.8 (C5), 145.5 (C9), 144.4 (C2) 132.1 (C4), 131.3 (C6), 127.1 (C7), 125.4 (C3), 120.6 (C5 or C8), 114.7 (C5 or C8), 113.9 (C4).

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, 1-(Methylsulfonyl)-1H-benzo[d][1,2,3]triazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; UNIVERSITY OF SUNDERLAND; TODD, Adam; ANDERSON, Rosaleen Joy; SMALL, David Antony Philip; GROUNDWATER, Paul William; BENTON, Matthew Richard; WO2014/96864; (2014); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

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. 402-46-0, name is 4-Fluorobenzenesulfonamide, A new synthetic method of this compound is introduced below., HPLC of Formula: C6H6FNO2S

General procedure: A dry round bottom flask was cooled to rt under nitrogen, and was charged with Pd2(dba)3 (3.38mg, 0.0037mmol), cesium carbonate (361mg, 1.11mmol), and arenesulfonamide (69mg, 0.44mmol). Tertiary-butanol (2mL) was added, followed by ligand, xantphos (6.4mg, 0.011mmol) and 9-chloroacridine (80mg, 0.37mmol). The resulting suspension was stirred at rt for 5min, then heated to 80C for 12-17h. The reaction mixture was then cooled to rt and filtered through suction filtration. The organic fraction was evaporated, and the resulting residue was purified by silica gel chromatography with a hexane/Et-OAc as eluent (60:40).

The synthetic route of 402-46-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Chourasiya, Sumit S.; Wani, Aabid A.; Nagaraja; Chakraborti, Asit K.; Bharatam, Prasad V.; Tetrahedron; vol. 74; 27; (2018); p. 3634 – 3641;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Electric Literature of 1888-91-1, A common heterocyclic compound, 1888-91-1, name is N-Acetylcaprolactam, molecular formula is C8H13NO2, 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.

General procedure: Under an argon atmosphere, liquid NH3 (25 mL) was condensedin a two-neck round-bottom flask immersed in a dry ice coolingbath and equipped with a dry ice reflux condenser. Aldehyde(7.34 mmol) was added, and the resulting solution (or suspension)was stirred for 1 h. KMnO4 (7.34 mmol, 1.16 g) was added,the cooling bath was removed, and the reaction mixture wasstirred for another hour with gentle reflux of NH3. Na2SO3 (22.0mmol, 2.78 g) was added, the reflux condenser was removed,and the NH3 was allowed to evaporate spontaneously. The darkbrownresidue was treated with 6 M HCl (30 mL), and theresulting precipitate was filtered, washed with H2O (100 mL)and sat. aq NaHCO3 (20 mL). All products were recrystallizedfrom EtOH.

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:
Article; Antoniak, Damian; Sakowicz, Arkadiusz; Loska, Rafal; Makosza, Mieczyslaw; Synlett; vol. 25; 9; (2014);,
Amide – Wikipedia,
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Some common heterocyclic compound, 103361-99-5, name is 7-Fluoro-2H-benzo[b][1,4]oxazin-3(4H)-one, molecular formula is C8H6FNO2, 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. Formula: C8H6FNO2

To a stirred solution of step 2 intermediate (2.7 g, 16.157 mmol) in sulphuric acid (3 ml) a mixture of nitric acid (69 %, 0.72 ml, 16.157 mmol) and concentrated sulphuric acid (2 ml) was drop wise added at 0 C under nitrogen atmosphere. The reaction mixture was stirred at 0 C for 30 min. The reaction mixture was quenched with ice-cooled water and solid was precipitated. The precipitated solid was dissolved in ethyl acetate (30 ml) and washed with aqueous saturated solution of sodium bicarbonate (150 ml). The ethyl acetate layer was dried and filtered and dried (Na2S04) and concentrated to yield 2.6 g of product as yellow solid. 1H NMR (300 MHz, DMSO-d6) delta 4.79 (s, 2H), 7.26 (d, J = 12.0 Hz, 1H), 7.63 (d, / = 7.2 Hz, 1H), 1 1.03 (br s, 1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 103361-99-5, its application will become more common.

Reference:
Patent; GLENMARK PHARMACEUTICALS S.A.; CHAUDHARI, Sachin Sundarlal; KUMAR, Sukeerthi; THOMAS, Abraham; KHAIRATKAR-JOSHI, Neelima; SHAH, Daisy Manish; WO2013/153539; (2013); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

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. 75175-77-8, name is 3-(4-Fluorophenyl)-N,N-dimethylacrylamide, A new synthetic method of this compound is introduced below., SDS of cas: 75175-77-8

General procedure: With a mixture of N,N-Dimethylenaminones 1 (1.0 mmol), isatins 2 (0.5 mmol), ammonium acetate 3 (1.0 mmol) in AcOH (1 mL) and EtOH-water (1:4) (5 mL), the reaction mixture was stirred at 80 C for 6 h until TLC indicated that the reaction was completed. The reaction mixture was allowed to cool to room temperature, neutralised with a saturated solution of Na2CO3 to pH 8-9, and then was extracted with ethyl acetate (2 ¡Á 30 mL). The organic phase was washed with water (20 mL) and the organic layer dried over Na2SO4, and concentrated under reduced pressure. The crude product was chromatographed onsilica gel (200-300 mesh) using a mixture of petroleum ether and ethyl acetate as eluent to afford the product 4.

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:
Article; Zhou, Pan; Hu, Biao; Lu, Lingling; Huang, Rong; Yu, Fuchao; Journal of Chemical Research; vol. 41; 9; (2017); p. 513 – 516;,
Amide – Wikipedia,
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Application of 1943-79-9,Some common heterocyclic compound, 1943-79-9, name is Phenyl methylcarbamate, molecular formula is C8H9NO2, 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.

To a solution of (2R,4S,4aS)-8-amino-2,4-dimethyl-l,2,4,4a-tetrahydro-2’H,6H-spiro[l,4- oxazino[4,3-a]quinoline-5,5′-pyrimidine]-2′,4′,6′(leta,3eta)-trione (Intermediate 34, 250 mg, 0.74 mmol) in anhydrous THF (20 mL) at 0 0C was added triethylamine (2.5 g, 0.024 mol) followed by methylphenoxycarbamate (0.66 mmol) and the mixture was refluxed for 48 hours. Methyl phenoxy carbamate was prepared by stirring methyl amine (1 eq.) and phenylchloro formate (1 eq.) in DCM at -30 0C to room temperature for 4 hours, and was purified by column chromatography. The reaction mixture was quenched with HCl (IN, 30 ml) and extracted with ethyl acetate (5 x 20 mL). The organic phase was dried over anhydrous sodium sulphate and was concentrated under reduced pressure. The residue thus obtained was washed with ether and further purified by preparative TLC to give the title compound. Yield: 20 mg (70%). MS(ES) MH+: 402.2 for Ci9H23N5O5 1H NMR (400 MHz, DMSO-d6) delta : 0.9 (d, 3H), 1.1 (d, 3H), 2.5 (d, 3H), 2.9 (d, IH), 3.1 (d, IH), 3.5 (d, IH), 3.55 (m, 2H), 3.85 (d, IH), 5.8 (m, IH), 6.7 (d, IH), 6.9 (s, IH), 7.1 (d, IH), 11.7 (bs, 2H).

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

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2009/4382; (2009); A2;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Synthetic Route of 144912-84-5, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 144912-84-5 name is tert-Butyl (3-amino-2-hydroxypropyl)carbamate, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

The obtained crude product of ((S)-3-amino-2-hydroxypropyl)carbamic acid tert-butyl ester (283 mg, 1.487 mmol) and 5-[2-amino-6-(3-carboxylpropylsulfanyl)pyrimidin-4-yl]-2,4-dimethylbenzoic acid tert-butyl ester (300 mg, 0.744 mmol) obtained in Step 1 of Example 2-1 were dissolved in N,N-dimethylformamide (7 ml), and then 1-hydroxybenzotriazole monohydrate (377 mg, 2.462 mmol) and 1-ethyl-3-(3′-dimethylaminopropyl)carbodiimide hydrochloride (152 mg, 2.2 mmol) were sequentially added thereto. The resulting mixture was stirred at room temperature for three hours. The reaction solution was diluted with ethyl acetate, and then washed with a saturated aqueous ammonium chloride solution (twice) and a saturated aqueous sodium bicarbonate solution (twice). After the organic layer was dried over anhydrous sodium sulfate, the inorganic salt was removed by filtration. The filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (developing solvent: dichloromethane:methanol = 20:1) to yield ((S)-3-amino-2-hydroxypropyl)carbamic acid tert-butyl ester. The obtained ((S)-3-amino-2-hydroxypropyl)carbamic acid tert-butyl ester was dissolved in dichloromethane (20 ml), and then water (0.1 ml) and trifluoroacetic acid (10 ml) were added thereto. After the solution was stirred at room temperature for one hour, the solvent was distilled off under reduced pressure to yield a crude product of 5-{2-amino-6-[2-((R)-3-amino-2-hydroxypropylcarbamoyl)ethylsulfanyl]pyrimidin-4-yl}-2,4-di methylbenzoic acid di(trifluoroacetate).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, tert-Butyl (3-amino-2-hydroxypropyl)carbamate, and friends who are interested can also refer to it.

Reference:
Patent; Chugai Seiyaku Kabushiki Kaisha; EP2119718; (2009); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 152192-95-5, name is tert-Butyl ethyl(2-hydroxyethyl)carbamate, 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 152192-95-5, COA of Formula: C9H19NO3

To a mixture of tert-butyl ethyl(2-hydroxyethyl)carbamate (1.89 g) obtained in Reference Example 19 and ethyl acetate (20 mL) were added acetic anhydride (1.04 mL), pyridine (0.89 mL) and 4-dimethylaminopyridine (0.061 g). After stirring at room temperature for 3 hrs., ethyl acetate (50 mL) was added, and the mixture was washed with water (50 mL), a 5% aqueous citric acid solution (50 mL) and saturated brine (50 mL). After drying over anhydrous magnesium sulfate, the mixture was concentrated under reduced pressure. A 4N hydrogen chloride – ethyl acetate solution (10 mL) was added to the residue, and the mixture was stirred at room temperature for 1 hr. Ethyl acetate (10 mL) and diethyl ether (20 mL) were added, and the precipitated solid was collected by filtration. The solid was dried under reduced pressure to give the title compound (1.54 g) as a white solid.1H-NMR(DMSO-d6) : 1.22 (3H,t,J=7.3Hz), 2.07 (3H,s), 2.95(2H,q,J=7.3Hz), 3.15(2H,t,J=5.3Hz), 4.24-4.30(2H,m), 9.17 (2H,br).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, tert-Butyl ethyl(2-hydroxyethyl)carbamate, and friends who are interested can also refer to it.

Reference:
Patent; Takeda Pharmaceutical Company Limited; EP1607088; (2005); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Reference of 683-57-8, 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. 683-57-8, name is 2-Bromoacetamide belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a solution of 5-bromo-2-hydroxybenzonitrile 1 (1O g, 50.5 mmol) in 50 mL acetone was added potassium carbonate (13.8 g, 100 mmol) and 2- bromoacetamide (6.9 g, 50.5 mmol). The reaction mixture was heated to 60 0C for 18 hours. After cooling, the solids were filtered off and dissolved in a large excess of water (1000 mL). The white solid was collected and dried to afford 11.2 g (89%) of 2- (4-bromo-2-cyanophenoxy)acetamide 2 as a white solid. 1H NMR (400 MHz, d6- DMSO): 8.03 (d, IH), 7.83 (dd, IH), 7.53 (br s, 1 H), 7.45 (br s, IH), 7.03 (d, IH), 4.7 (s, 2H).

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, 2-Bromoacetamide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; EXELIXIS, INC.; WO2009/86264; (2009); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

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. 402-46-0, name is 4-Fluorobenzenesulfonamide, This compound has unique chemical properties. The synthetic route is as follows., Safety of 4-Fluorobenzenesulfonamide

Example 14 31. N-(4-fluorophenyl)sulfonyl-a-dehydrocyclohexylglycine.; 2-cyclohexyl-2-oxoethanoic acid (3.0 g, 19.2 mmol) was combined with p-toluenesulfonamide (2.70 g, 15.4 mmol) in toluene (21 mL) and diethyleneglycol diethyl ether (3 mL). MSA (0.10 mL, 1.5 mmol) was added, and this mixture was heated at reflux for 28h, then cooled to rt. The resulting solids were mixed with EtOAc (35 mL) and NaHC03 (2.6 g) in water (60 mL), until all materials dissolved. The aqueous was separated, and the organics were washed with NaH C03 (0.40 g) in water (10 mL). The combined aqueous layer was then washed with EtOAc (20 mL). The aqueous layer was cooled to 0 C, then treated with HCl (12.1 N, 3.1 mL). The resulting solids were filtered and washed with water and dried to give 3.0 g of crude material. The solids were then recrystallized from toluene/ methanol to give 2.8 g of white solid (58% yield). mp 214-215 C. ?H-NMR (400 MHz, CD30D) d 7.83-7.88 (m, 2H), 7.23-7.29 (m, 2H), 2.61-2.65 (m, 2H), 2.21-2.24 (m, 2H), 1.55-1.59 (m, 4H), 1.41-1.46 (m, 2H); ?3C NMR (100 MHz, CD30D) 167.2, 166.3,163.7, 155.3,136.5 (2 peaks), 129.9 (2 peaks), 118.3,115.5, 115.3,31.0, 30.5, 27.6, 27.2,25.7 ppm. HRMS calcd for C14H15FN04S (M-H) : 312.0706, Found: 312.0707.

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 402-46-0.

Reference:
Patent; MERCK & CO., INC.; WO2005/118529; (2005); A2;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics