Month: December 2020

68524-30-1, 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. 68524-30-1, name is 2-[(Diphenylmethyl)thio]acetamide belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Asymmetric synthesis of (-)-2-(diphenylmethyl)sulphinylacetamideGeneral procedure for examples 1 to 10 : Diphenylmethylthioacetamide (7.70 g ; 0.03 mol ; 1.0 eq) was dissolved in the solvent (toluene ; 77 mL ; 10 vol.) under argon. To the solution were added (S,S)-(-)-diethyl-tartrate (1.23 g ; 0.006 mol; 0.2 eq) and titanium (IV) tetraisopropoxide (0.85 g ; 0.88 mL ; 0.003 mol; 0.1 eq) and water (27 muL minus the sum of water present in reactants and solvent already introduced ; 0.0015 mol ; 0.05 eq) at 55C. In these conditions, the resulting chiral titanium complex has the stoichiometry (DET/Ti(OiPr)4/H2O : 2/1/0.5) and represents 0.1 eq of diphenylmethylthioacetamide. Stirring was maintained at 55C during 50 minutes. After cooling to room temperature (25C), were added to the mixture diisopropylethylamine (0.39 g ; 0.52 mL ; 0.003 mol ; 0.1 eq) and cumene hydroperoxide (4.55 g ; 5.0 mL ; 0.03 mol ; 1.0 eq). After contacting during about an hour, the formed precipitate is isolated by filtration. All the following experiments were performed in accordance with the conditions of the general procedure, by modifying parameters as indicated in tables 1-10.; Example 2 : Influence of the amount of water on the enantioselectivity of asymmetric oxidation In this experiment, the ratio of water was varied with respect to the titanium tetraisopropoxide from 0 to 1 equivalent, all the other parameters being as defined in the above general procedure. Notably, the ratio of the titanium chiral complex was maintained at 0.1 equivalent with respect to the diphenylmethylthioacetamide. [Table 2] EntryAmount of water (equivalent)E. e. (%)Purity (%)Yield (%)1080-90.320.493> 999230.894> 9988419199.590 – = Not determined These results show that the amount of water has an effect on the enantioselectivity of the reaction. Thus, the best enantioselectivities are achieved when an amount of water comprised between 0.4 and 0.8 equivalents are used. On the opposite, the enantioselectivity drops notably in the absence of water.

The synthetic route of 2-[(Diphenylmethyl)thio]acetamide has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CEPHALON FRANCE; EP1516869; (2005); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

239074-29-4, The chemical industry reduces the impact on the environment during synthesis 239074-29-4, name is tert-Butyl (trans-4-(hydroxymethyl)cyclohexyl)carbamate, I believe this compound will play a more active role in future production and life.

Trans (4-Amino-cyclohexyl)-acetonitrileTrans Methanesulfonic acid 4-tert-butoxycarbonylamino-cyclohexylmethyl esterTrans (4-hydroxymethyl-cyclohexyl)-carbamic acid tert-butyl ester (3.49 g, 15.0 mmol) in DCM (50 mL) was treated with pyridine (4.98 mL, 60.8 mmol). The mixture was cooled to 0 C and methanesulfonyl chloride (2.36 mL, 30.4 mmol) was added dropwise over 5 minutes. The mixture was stirred at room temperature for 5 hours and then concentrated under vacuum. The residue was partitioned between ethyl acetate and water and the aqueous phase extracted with ethyl acetate (x2). The combined organic extracts were washed with brine, dried with sodium sulfate and concentrated under vacuum. The residue was triturated with cyclohexane then dried under vacuum to give a white solid. Further purification by column chromatography on silica gel (eluting with 1 : 1 cyclohexane/ethyl acetate) gave 4.17 g (90%) of trans methanesulfonic acid 4- tert-butoxycarbonylamino-cyclohexylmethyl ester as a white solid. 1H NMR (400 MHz, CDCI3) delta: 4.37 (br s, 1 H), 4.02 (d, 2 H), 3.39 (br s, 1 H), 3.00 (s, 3 H), 2.11-2.00 (m, 2 H), 1.91-1.81 (m, 2 H), 1.77-1.64 (m, 1 H), 1.43 (s, 9 H), 1.18-1.05 (m, 4 H).

The chemical industry reduces the impact on the environment during synthesis tert-Butyl (trans-4-(hydroxymethyl)cyclohexyl)carbamate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HURLEY, Christopher; KULAGOWSKI, Janusz; ZAK, Mark; WO2013/7768; (2013); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

6292-59-7, 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. 6292-59-7, name is 4-(tert-Butyl)benzenesulfonamide, A new synthetic method of this compound is introduced below.

EXAMPLE 9; Synthesis of 2-[6-(4-tert-Butyl-benzenesulfonylamino)-5-(2-methoxy-phenoxy)-[2,2′]bipyrimidinyl-4-yloxy]-ethanol acetyl ester; In a 3000 ml round-bottom flask under nitrogen atmosphere, 4-tert-butyl-benzenesulfonamide (103 g, 0.480 mol) and potassium carbonate (166 g, 1.200 mol) are suspended in N,N-dimethyl-acetamide (300 ml) and acetonitrile (200 ml) and the mixture is heated at 75-80¡ã C. for about 30 minutes. The reaction mixture is cooled to about 65-70¡ã C. and added with 2-(5-(2-methoxy-phenoxy)-6-chloro-2-(pyrimidin-2-yl)pyrimidin-4-yloxy)ethanol acetyl ester (200 g, 0.480 mol). The mixture is reacted for 96 hours then diluted with water (1500 ml) and cooled at 0-5¡ã C. for at least 1 hour. The solid is filtered, washing with cold water (4.x.250 ml), and dried at about 45-50¡ã C. for 16-18 hours. 213 g of a solid crude are obtained, in 75percent yield. The resulting product is used for the next reaction, as described in Example 7.

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; Dipharma Francis S.r.l.; US2009/156811; (2009); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 6331-71-1, name is 4-Amino-N,N-dimethylbenzamide, 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 6331-71-1, 6331-71-1

EXAMPLE 22 A mixture of 9 parts of 4-amino-N,N-dimethylbenzamide, 137 parts of concentrated hydrochloric acid and 90 parts of water was stirred at room temperature. 21.6 Parts of a hydrogen peroxide solution 30% in water were added and the whole was stirred for 4 hours at room temperature. The product was extracted three times with dichloromethane. The combined extracts were dried, filtered and evaporated. The residue was purified by column chromatography over silica gel using a mixture of trichloromethane and methanol (98:2 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was crystallized from 2,2′-oxybispropane. The product was filtered off and dried, yielding 5.78 parts (46%) of 4-amino-3,5-dichloro-N,N-dimethylbenzamide; mp. 134.2 C. (int. 110).

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, 4-Amino-N,N-dimethylbenzamide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Janssen Pharmaceutica N.V.; US4880808; (1989); A;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 1118-69-0, name is N-Isopropylacetamide, 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 1118-69-0, 1118-69-0

Preparation of Zr(LMeJPr)4 (28). A 100 ml_ Schlenk flask, fitted with a reflux condenser, was charged with tetrakis(dimethylamido)zirconium (0.200 g, 0.748 mmol) and toluene (10 ml_). A solution of LMe iotaPrH (0.302 g, 2.99 mmol) in toluene (10 ml_) was added slowly and the resultant mixture was refluxed for 3 h. Upon cooling to room temperature, the volatile components were removed under reduced pressure and sublimation of the crude solid at 110 C/0.05 Torr afforded 28 as colorless crystals (0.188 g, 51 %): mp 206-209 0C.

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, N-Isopropylacetamide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; WAYNE STATE UNIVERSITY; WINTER, Charles, H.; KNISLEY, Thomas, Joseph; KARUNARATHNE, Panditha Koralalage, Don Mahesh Chinthaka; WO2010/132871; (2010); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

3984-14-3, 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. 3984-14-3, name is N,N-Dimethylsulfamide, This compound has unique chemical properties. The synthetic route is as follows.

1,1′-Carbonyldiimidazole (1.17 g, 7.2 mmol) was added to a stirred solution of 2-bromo-3-cyclohexyl-1H-indole-6-carboxylic acid (2.03 g, 6.3 mmol) in THF (6 mL) at 22 C. The evolution of CO2 was instantaneous and when it slowed the solution was heated at 50 C. for 1 hr and then cooled to 22 C. N,N-Dimethylsulfamide (0.94 g, 7.56 mmol) was added followed by the dropwise addition of a solution of DBU (1.34 g, 8.8 mmol) in THF (4 mL). Stirring was continued for 24 hr. The mixture was partitioned between ethyl acetate and dilute HCl. The ethyl acetate layer was washed with water followed by brine and dried over Na2SO4. The extract was concentrated to dryness to leave the title product as a pale yellow friable foam, (2.0 g, 74%, >90% purity, estimated from NMR). 1H NMR (300 MHz, DMSO-D6) delta ppm 1.28-1.49 (m, 3H) 1.59-2.04 (m, 7H) 2.74-2.82 (m, 1H) 2.88 (s, 6H) 7.57 (dd, J=8.42, 1.46 Hz, 1H) 7.74 (d, J=8.78 Hz, 1H) 7.91 (s, 1H) 11.71 (s, 1H) 12.08 (s, 1H).An alternative method for the preparation of 1H-indole-6-carboxamide, 2-bromo-3-cyclohexyl-N-[(dimethylamino)sulfonyl]- is described below.To a 1 L four necked round bottom flask equipped with a mechanical stirrer, a temperature controller, a N2 inlet, and a condenser, under N2, was added 2-bromo-3-cyclohexyl-1H-indole-6-carboxylic acid (102.0 g, 0.259 mol) and dry THF (300 mL). After stirring for 10 min, CDI (50.3 g, 0.31 mol) was added portion wise. The reaction mixture was then heated to 50 oC. for 2 h. After cooling to 30 oC., N,N-dimethylaminosulfonamide (41.7 g, 0.336 mol) was added in one portion followed by addition of DBU (54.1 mL, 0.362 mol) drop wise over a period of 1 h. The reaction mixture was then stirred at rt for 20 h. The solvent was removed in vacuo and the residue was partitioned between EtOAc and 1 N HCl (1:1, 2 L). The organic layer was separated and the aqueous layer was extracted with EtOAc (500 mL). The combined organic layers were washed with brine (1.5 L) and dried over MgSO4. The solution was filtered and concentrated in vacuo to give the crude product (111.0 g). The crude product was suspended in EtOAc (400 mL) at 60 oC. To the suspension was added heptane (2 L) slowly. The resulting suspension was stirred and cooled to 0 oC. It was then filtered. The filter cake was rinsed with small amount of heptane and house vacuum air dried for 2 days. The product was collected as a white solid (92.0 g, 83%). 1H NMR (MeOD, 300 MHz) delta 7.89 (s, H), 7.77 (d, J=8.4 Hz, 1H), 7.55 (dd, J=8.4 and 1.8 Hz, 1H), 3.01 (s, 6H), 2.73-2.95 (m, 1H), 1.81-2.05 (m, 8H), 1.39-1.50 (m, 2H); m/z 429 (M+H)+.

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; Bristol-Myers Squibb Company; US2009/130056; (2009); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

711007-44-2, Adding some certain compound to certain chemical reactions, such as: 711007-44-2, name is 2,3-Diaminobenzamide, 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 711007-44-2.

To a 100 ml three-neck flask was added 2,3-diaminobenzamide (3.2 g, 20 mmol), compound C (4.47 g, 22 mmol), sulfur powder (3.2 g, 100 mmol) was added, and stirred at 170 C. After 6 h, after cooling, 60 ml of methylene chloride was added to dissolve, and the silica gel was mixed and concentrated on a silica gel column. Chromatography on a silica gel column afforded the target product (C3) 0.76 g (yield: 11%).

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 711007-44-2.

Reference:
Patent; Shandong University Qilu Hospital; Tan Bingxu; (9 pag.)CN107556288; (2018); A;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

The chemical industry reduces the impact on the environment during synthesis 711007-44-2, name is 2,3-Diaminobenzamide, I believe this compound will play a more active role in future production and life. 711007-44-2

General procedure: In a dark environment, a mixture of 2,3-diaminobenzamide(1.51 g, 10 mmol), PYTZ (20 mg), and ethanol (200 mL)was taken in an open pear-shaped bottle, stirred magneticallyat room temperature, and then aldehyde (10 mmol) wasadded slowly in 2 min. The bottle was exposed to visiblelight (Xenon, 10 A) under stirring condition. The reactionwas monitored by TLC. After the reaction completed, thereaction mixture was transferred to a three-neck bottle outsideof the photochemical reactor and air was introduced toensure that the intermediate was completely oxidized. Then,the solvent was evaporated in vacuum to 40 mL until thesolid appeared. The mixture was cooled down in an ice bathfor crystallization, filtration. The crude solid was recrystallizedfrom 25 mL ethanol (30 C) to get the target products.

The chemical industry reduces the impact on the environment during synthesis 711007-44-2. I believe this compound will play a more active role in future production and life.

Reference:
Article; Zhang, Li-Jie; Yang, Kang; Li, Chun-Yu; Sun, Ya-Quan; Chemical Papers; vol. 73; 11; (2019); p. 2697 – 2705;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

749927-69-3, 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. 749927-69-3, name is 4-Bromo-2-fluoro-N-methylbenzamide, This compound has unique chemical properties. The synthetic route is as follows.

Copper chloride (12.8 gm) was charged to N,N?-dimethyl Formamide (600 ml) under argon atmosphere at 75-80C. 4-Bromo-2-fluoro-N-methylbenzamide obtained in example 1 (100 g) was charged to the mixture followed by addition of N,N-dimethylaniline (8.35 gm). The reaction mixture was stirred for 15-20 minutes. 2-aminoisobutyric acid (67 gm) was added and again the mixture was stirred for 15-20 minutes at 75-80C. Powdered potassium carbonate (148 gm) was added and stirred for 15 minutes. Water (10 ml) was added and the temperature of the mass was raised to 1 l0C and the mass was stirred for 4- 5 hours at 4-5 hours. The mass was cooled to 30-35C and filtered. The mass was filtered and washed with dimethyl formamide. Dimethyl formamide was distilled out under vacuum and the mass was cooled. Water (700 ml) was added to the mass and pH was adjusted to 13.5 – 14 by using 10% sodium hydroxide solution. MDC (300 ml) was added to the reaction mass and stirred. The layers were separated and aqueous layer was extracted with MDC (300 ml). MDC layer was separated and washed with water (300 ml). All the aqueous layers were combined and pH was adjusted to 2.5-3 by HC1 to precipitate out the product. The mass was stirred and filtered under vacuum. The precipitate was washed with water (100 ml) and suck dried well. The material was dried under vacuum at 55-60C.The dried product 2-[3-fluoro-4-(methylcarbamoyl) anilino]-2-methyl-propanoic acid (135 g) was isolated. Thereafter, the product is tested for HPLC purity which was observed to be 99.4%.

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; AARTI INDUSTRIES LIMITED; DESAI, Parimal Hasmukhlal; SEETHARAMAN, Subramanian; NIKAM, Vikas Hiraman; KAMBLE, Kiran Mohan; (73 pag.)WO2019/106691; (2019); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

57561-39-4, 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. 57561-39-4, name is tert-Butyl (2-hydroxyethyl)(methyl)carbamate, A new synthetic method of this compound is introduced below.

To a well-stirred solution of N-Boc-N-Me-glycinol (3.5 g, 20 mmol) in DMSO (20 mL) cooled with an ice-water bath was add allyl bromide (3.6 g, 30.0 mmol), followed by finely ground KOH powder (3.5 g, 30.0 mmol) over 15 minutes. The resulting solution was stirred for overnight at room temperature. The resulting mixture was partitioned between 5% aq. HOAc (50mL) and ethyl acetate (200ml). The organic layer was separated, washed with brine, dried with sodium sulfate, filtered, and concentrated, then purified by flash chromatography eluting with 10% to 80% ethyl acetate/hexane. Yield of product 4.1g, 95%. Ion(s) found by LCMS: M+H =216.3.

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; CIDARA THERAPEUTICS, INC.; BALKOVEC, James, M.; BENSEN, Daniel, C.; BORCHARDT, Allen; BRADY, Thomas, P.; CHEN, Zhi-Yong; COLE, Jason; DO, Quyen-Quyen, Thuy; DOEHRMANN, Simon; JIANG, Wanlong; LAM, Thanh; NONCOVICH, Alain; TARI, Leslie, W.; (797 pag.)WO2020/51498; (2020); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics