Month: February 2021

Adding a certain compound to certain chemical reactions, such as: 7150-72-3, name is tert-Butyl vinylcarbamate, 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 7150-72-3, Recommanded Product: 7150-72-3

4-Fluorophenyl benzaldehyde-tosylhydrazone sodium salt (786 mg, 2.5 mmol), N-vinyl-carbamic acid tert-butyl ester (1.432 g, 10 mmol) and benzyltriethylammonium chloride (57 mg, 0.25 mmol) were covered with dioxane (11 ml) under argon. Rh2(OAc)4 (11 mg, 0.025 mmol) was added and the suspension stirred at room temperature for 15 minutes. The slurry became thick and difficult to stir so a further 4 ml of dioxane was added. The mixture was stirred at 75 C. for 2 hours, then shaken between tBuOMe and water. The organic phase was washed with water and NaCl (satd), dried over MgSO4 and evaporated to yield a brown viscous oil (1.353 g), which was chromatographed on silica to yield 2-(4-fluoro-phenyl)-cyclopropyl-carbamic acid tert-butyl ester 369 mg (59%, m.p. 117-118 C.) cis and 125 mg (20% m.p. 102-105 C.) trans. 1H-NMR (CDCl3, signals for the cis isomer) 0.93 (1H, m), 1.32 (9H, s), 2.20 (1H, m), 2.89 (1H, m), 4.23 (1H, m), 6.98 (2H, t), 7.18 (2H, t).

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

Reference:
Patent; SYNGENTA PARTICIPATIONS AG; O’Sullivan, Anthony Cornelius; Loiseleur, Olivier; Stierli, Daniel; Luksch, Torsten; Pitterna, Thomas; US2014/378461; (2014); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Application of 77925-80-5, A common heterocyclic compound, 77925-80-5, name is N-(Benzyloxy)-2-nitrobenzenesulfonamide, molecular formula is C13H12N2O5S, 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.

2S,5S)-1-(tert-butyl) 2-ethyl 5-hydroxylpiperidine-1,2-dicarboxylate (130 g, 475.62 mmol), triphenylphosphine (212 g, 809.16 mmol) and N-(benzyloxy)-2-nitrophenyl-1-sulfamide (161.4 g, 523.5 mmol) were dissolved in tetrahydrofuran (1500 mL), cooled to 0C, diethyl azodicarboxylate (149.1 g, 856.16 mmol) was added dropwise under nitrogen gas protection, after adding, the reaction solution was heated to room temperature and stirred overnight, concentrated, and the crude product was purified by silica gel chromatograph (ethyl acetate : petroleum ether = 1:5) to obtain the title compound as a yellow oil (210 g, yield 78%).

The synthetic route of 77925-80-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Xuanzhu Pharma Co., Ltd.; WU, Frank; (77 pag.)EP3281942; (2018); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Electric Literature of 1129-26-6,Some common heterocyclic compound, 1129-26-6, name is 4-Methoxybenzenesulfonamide, molecular formula is C7H9NO3S, 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: To a stirred solution of the intermediates compound2a-2d (1 mmol) with triethylamine (2 mmol) into DMF(12 mL), then a mixture of 1-ethyl-(3-(3-dimethylamino)-propyl)-carbodiimide hydrochloride (EDCI) (1 mmol) andN-hydroxybenzotriazole (HOBt) (1 mmol) was placed in thereaction system, stirred at room temperature for 30 min, themixture of substituted benzene sulfonamide (1 mmol) andDMF (5 mL) was added in the reaction system, the reactionmixture was monitored by TLC. After completion of the reaction,the product was extracted from chloroform with water,0.2 mol/L hydrochloric acid, water, 2.0 mol/L sodium hydroxide,saturated sodium chloride successively, and then dried,concentrated, and purified by preparative thin layer chromatographyfollowed by recrystallization from ethanol.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Methoxybenzenesulfonamide, its application will become more common.

Reference:
Article; Lv, Xian-Hai; Ren, Zi-Li; Liu, Hao; Li, Hai-Dong; Li, Qing-Shan; Wang, Li; Zhang, Li-Song; Yao, Xiao-Kang; Cao, Hai-Qun; Chemical and Pharmaceutical Bulletin; vol. 66; 4; (2018); p. 358 – 362;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 406233-31-6, name is 4-Fluoro-3-nitrobenzenesulfonamide, 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 406233-31-6, Quality Control of 4-Fluoro-3-nitrobenzenesulfonamide

General procedure: To an ice cold stirred solution of compound 4a-4u (1 eq) in anhydrousDCM (10 mL for 1 mmol of substrate), TEA (3 eq) was added dropwise and stirred for 10 min. Compound 5 (1 eq) was added slowly andstirred at RT for 16 h (precipitation was observed during the reactionprogress). TLC showed completion of reaction. The reaction mixturewas concentrated under reduced pressure. Water was added to thecrude material and stirred for 30 min. Obtained solid was filtered,washed with water and dried under vacuum. The solid was trituratedwith ethyl acetate, filtered and dried under high vacuum to affordcompound 6a-v.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Fluoro-3-nitrobenzenesulfonamide, and friends who are interested can also refer to it.

Reference:
Article; Kalisha Vali; Gundla, Rambabu; Singh, Om V.; Tamboli, Yasinalli; Di Cesare Manelli, Lorenzo; Ghelardini, Carla; Al-Tamimi, Abdul-Malek S.; Carta, Fabrizio; Angeli, Andrea; Supuran, Claudiu T.; Bioorganic Chemistry; vol. 92; (2019);,
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. 22227-26-5, name is 3,5-Bis(trifluoromethyl)benzamide, A new synthetic method of this compound is introduced below., SDS of cas: 22227-26-5

Charged 3,5-bis(trifluoromethyl)benzonitrile (100 gm, 1 meq.), 2 (N) Sodium hydroxide (21.7 gm, 1.3 meq.) into 400 ml methanol and stirred the reaction mass at 20 – 30¡ãC for 2-3 hrs. Added Dimethyl sulphoxide (100 ml) followed by dilute 30percent H202 solution (100 gm diluted in 300m1 water, 2.1 eq.) at 20 -35¡ãC. Stirred the mass for 2-3 hrs. at 20-30¡ãC and confirmed reaction completion by HPLC. Reaction mass quenched by addition of water (500 ml, S Vol). Filtered the slurry and washed the wet cake by water (500 ml, SVol). Dried under vacuum at 50-60¡ãC to get 100 gm 3, 5-bis (trifluoromethyl) benzamide (Purity 99 percent). Charged 3, 5-bis (trifluoromethyl) benzamide, prepared according to procedures a or b, as described above, (100 gm, 1 meq) into N, N Dimethyl formamide (100 ml, 1 vol). Added N, N Dimethyl formamide dimethyl acetal (70 gm, 1.5 meq) at 20-30¡ãC and stirred the reaction mass for 2-3 hrs. Reaction completion for the formation N-((dimethylamino)methylene)-3,5- bis(trifluoromethyl)benzamide was confirmed by HPLC. Cooled reaction mass to 10-15¡ãC and added acetic acid (S00 ml, S vol.) followed by hydrazine hydrate (31 gm, 1.5 meq). Reaction mass was heated to S0-SS¡ãC and stirred for 2-3 hrs. at same temparature. Reaction was monitored by HPLC. Cooled reaction mass to 20-30¡ãC and quenched by addition of water (2.S L, 2S vol.). Filtered the slurry and washed the wet cake by water (S00 ml, S vol.). Dried under vacuum at 50-60¡ãC to get 3 -(3,5 -bis(trifluoromethyl)phenyl)- 1 H-i ,2,4-triazole (94 gr, Purity 97percent).

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; WATSON LABORATORIES INC.; MUTHUSAMY, Anantha Rajmohan; KANNIAH, Sundara Lakshmi; RAVI, Akash; DAS, Tonmoy Chitta; CHEMATE, Rajendra Popat; SINGH, Anil Kumar; WAGH, Yogesh Dhananjay; (60 pag.)WO2018/129227; (2018); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

These common heterocyclic compound, 147751-16-4, name is tert-Butyl methylsulfonylcarbamate, 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. Quality Control of tert-Butyl methylsulfonylcarbamate

To a solution of benzyl 4-(hydroxymethyl)-3,3-dimethyl-pyrrolidine-1-carboxylate (300 mg, 1.14 mmol), tert-butyl N-methylsulfonylcarbamate (330 mg, 1.7 mmol) and PPh3 (890 mg, 3.4 mmol) in THF (20 mL) was added DEAD (390 muL, 2.5 mmol) dropwise and the reaction mixture stirred at ambient temperature under N2 for 16 hours. The reaction mixture was concentrated in vacuo and the residue purified by column chromatography (silica, 0 to 50% EtOAc/PE gradient elution) to give benzyl 4-[[tert- butoxycarbonyl(methylsulfonyl)amino]methyl]-3,3-dimethyl-pyrrolidine-1-carboxylate as a colourless oil that was taken directly on to the next step; MS m/z: 441 (M+H)+.

The synthetic route of tert-Butyl methylsulfonylcarbamate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK PATENT GMBH; VERTEX PHARMACEUTICALS INCORPORATED; BAYLY, Andrew; BLEICH, Matthew; CHARRIER, Jean-Damien; DODD, James; DURRANT, Steven; ENO, Meredith Suzanne; ETXEBARRIA I JARDI, Gorka; EVERITT, Simon; FRAYSSE, Damien; KELLY, Shazia; KNEGTEL, Ronald; MOCHALKIN, Igor; MORTIMORE, Michael; NORTH, Kiri; PORICHIS, Filippos; PULLIN, Robert; RUTHERFORD, Alistair; STORCK, Pierre-Henri; TWIN, Heather Clare; XIAO, Yufang; (1159 pag.)WO2019/148132; (2019); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Electric Literature of 78191-00-1,Some common heterocyclic compound, 78191-00-1, name is N-Methoxy-N-methylacetamide, molecular formula is C4H9NO2, 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 STIRRED solution of n-BuLi (2M in pentane ; 15.24 mL, 0.0305 mol) in 70 mL of dry ether at-78C was added dropwise 29 (6.3 g, 0.0277 mol) in 30 mL of ether over a period of 30 minutes. The mixture was stirred for lh, then N-methoxy-N-methylacetamide (3.83 mL, 0.036 mol) was added dropwise over 10 minutes. After lh of stirring at-78C the reaction mixture was washed with sat’d NAHCO3 and extracted with ether. The organic layer was dried with NA2S04 and concentrated in vacuo to give 6.66 g (89%) of 16 as an oil that was used directly for the next step.

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

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; WO2004/87699; (2004); A2;,
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. 37073-15-7, name is 1-(Methylsulfonyl)-1H-benzo[d][1,2,3]triazole, A new synthetic method of this compound is introduced below., Product Details of 37073-15-7

General procedure: A mixture of alpha,beta-unsaturated aromatic or aliphatic acid (10 mmol), CH3SO2Bt (10 mmol) and Et3N (15 mmol) were refluxed in dry THF (50 mL) overnight. The solvent was evaporated and the residue was dissolved in CH2Cl2 (100 mL). The organic phase was washed with brine (3 times) and dried over anhydrous Na2SO4. The organic phase was concentrated under vacuum to give a crude product, which could be further purified by recrystallization from a proper solvent.

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; Xia, Ziming; Lv, Xin; Wang, Wencun; Wang, Xiaoxia; Tetrahedron Letters; vol. 52; 38; (2011); p. 4906 – 4910;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Reference of 61903-11-5, These common heterocyclic compound, 61903-11-5, name is 1-(1,4-Diazepan-1-yl)ethanone, 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.

Lithium aluminum hydride (38.2 ml, 38.19 mmol) was added to 1-(1,4-diazepan-1-yl)ethanone (1.697 g, 11.93 mmol) in THF (59.7 ml) at 0 C. under nitrogen. The resulting solution was stirred at ambient temperature for 1 h and then at 60 C. for 1 h. The cooled reaction mixture was poured onto ice (500 mL), acidified with HCl (2M aqueous solution) and purified by ion exchange chromatography, using an SCX column. The desired product was eluted from the column using 7M NH3/MeOH and evaporated to dryness to afford 1-ethyl-1,4-diazepane (0.610 g, 40%) as a yellow liquid. This was used directly with no further purification. 1H NMR (399.9 MHz, CDCl3) delta 1.07 (3H, t), 1.74-1.80 (2H, m), 2.58 (2H, q), 2.64-2.70 (4H, m), 2.89-2.95 (4H, m).

Statistics shows that 1-(1,4-Diazepan-1-yl)ethanone is playing an increasingly important role. we look forward to future research findings about 61903-11-5.

Reference:
Patent; ASTRAZENECA AB; US2008/153812; (2008); 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. 78191-00-1, name is N-Methoxy-N-methylacetamide, A new synthetic method of this compound is introduced below., Quality Control of N-Methoxy-N-methylacetamide

To 2,7-dibromonaphthalene (1 g, 3.50 mmol) in anhydrous tetrahydrofuran (18 mL), at -78 C. and under an atmosphere of nitrogen, was added a solution of n-butyllithium (2.5 M in hexanes, 1.5 mL, 3.67 mmol) dropwise. The reaction was stirred at -78 C. for 20 min after which N-methoxy-N-methylacetamide (409 muL, 3.85 mmol) was added. After 15 min, the reaction was warmed to RT and stirred for 30 min. The reaction was quenched with 2 M hydrochloric acid and extracted twice with dichloromethane. The combined organic layers were dried through a hydrophobic frit and concentrated in vacuo. The product was purified by silica flash chromatography (iso-hexanes/ethyl acetate, 7/1) to afford the title compound (650 mg, 75%) as a colorless 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; Gilead Sciences, Inc.; Selcia Limited; Aciro, Caroline; Dean, David Kenneth; Dunbar, Neil Andrew; Highton, Adrian John; Jansa, Petr; Karki, Kapil Kumar; Keats, Andrew John; Lazarides, Linos; Mackman, Richard L.; Pettit, Simon N.; Poullennec, Karine G.; Schrier, Adam James; Siegel, Dustin; Steadman, Victoria Alexandra; (169 pag.)US2017/190737; (2017); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics