Tag: M.W=100-200

1943-79-9, The chemical industry reduces the impact on the environment during synthesis 1943-79-9, name is Phenyl methylcarbamate, I believe this compound will play a more active role in future production and life.

Sodium hydride (60% in oil, 228 mg, 5.7 mmol) was gradually added to a N,N-dimethylformamide (0.5 ml) solution of 5-nitroindole (0.841 g, 5.19 mmol) while stirring at room temperature; phenyl N-methylcarbamate (1.02 g, 6.74 mmol) was added thereto; and the reaction mixture was stirred overnight. The reaction mixture was partitioned between ethyl acetate and water; and the organic layer was washed with water and brine, dried over anhydrous sodium sulfate. This was concentrated under reduced pressure; and the residue was purified by silica gel column chromatography (hexane-ethyl acetate, sequentially ethyl acetate) to yield the title compound (600 mg). 1H-NMR Spectrum (DMSO-d6) delta (ppm): 2.88 (3H, d, J=4.4 Hz), 6.94 (1H, d, J=3.6 Hz), 8.03 (1H, d, J=3.6 Hz), 8.15 (1H, dd, J=2.4, 9.2 Hz), 8.35-8.43 (2H, m), 8.59 (1H, d, J=2.4 Hz).

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

Reference:
Patent; Eisai Co., Ltd.; EP1522540; (2005); 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. 49805-30-3, name is 2-Azabicyclo[2.2.1]hept-5-en-3-one, A new synthetic method of this compound is introduced below., 49805-30-3

1.5. Preparation of (+-)-1-amino-4-(hydroxymethyl)-2-cyclopentene in an alcohol A 100 ml round-bottom flask fitted with magnetic stirrer was charged with 3.0 g (27.5 mmol) of (+-)-2-azabicyclo[2.2.1]hept-5-en-3-one and 1.2 g (28.3 mmol) of lithium borohydride, under an inert-gas atmosphere, in 35 g of 2-butanol, and the mixture was stirred for 3 h at 60 C. GC analysis of a sample (work-up: 0.1 g sample rendered acidic using 0.2 ml of 1M HCl, then quickly rendered basic using 0.1 ml of saturated NaHCO3) indicated the formation of the product in 12% yield after this time. (GC standard is benzophenone.)

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; Lonza AG; US2002/10360; (2002); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

A common heterocyclic compound, 6274-22-2, name is 4-Amino-N-methylbenzamide, molecular formula is C8H10N2O, 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. 6274-22-2.

Step 1To a solution of 2, 4-dichloropyridine (0.500 g, 3.39 mmoL) and 4-amino-N- methylbenzamide (0.510 g, 3.39 mmoL) in dimethylacetamide (1 mL) was added cesium carbonate (1.6 g, 5.08 mmoL) and the reaction mixture was degassed for 15 min. Pd2(dba)3 (0.154 g, 0.169 mmol) and BINAP (105 mg, 0.169 mmol) were added and the reaction mixture was irradiated in the microwave at 120 C for 1 h. Then reaction was quenched with water and extracted with EtOAc (2 x 50 mL). The organic extracts were washed with brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. Purification by silica gel column chromatography provided 3-((4-chloropyridin-2-yl)amino)-N-methylbenzamide (0.300 g, 38%) as a solid. Observed mass (M+l): 262.1

The synthetic route of 4-Amino-N-methylbenzamide has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AMGEN INC.; BREGMAN, Howard; BUCHANAN, John, L.; CHAKKA, Nagasree; DIMAURO, Erin, F.; DU, Bingfan; NGUYEN, Hanh, Nho; ZHENG, Xiao, Mei; WO2011/103196; (2011); A1;,
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3119-02-6, 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. 3119-02-6, name is 4-Cyanobenzenesulphonamide belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a solution of 4-cyano benzenesulfonamide (3.8 g, 20.88 mmol, Intermediate 42 or commercial source: Combi-Blocks) in Lambda/,/V-dimethylformamide (50 mL), sodium azide (13.57 g, 208.73 mmol) and ammonium chloride (1 1.17 g, 208.78 mmol) were added at 27 C. The reaction mixture was heated to 120 C and was stirred at the same temperature for 5 h. Upon completion, the reaction mixture was cooled to 27 C, quenched with 1 N HCI (150 mL) and extracted with ethyl acetate (3×100 mL). The organic layer was dried over anhydrous Na2S04, filtered and the filtrate was concentrated under reduced pressure. The residue was stirred with dichloromethane (10 mL) at 27 C for 30 min and filtered. The solid was dried under vacuum to afford 4-(2H-tetrazol-5- yl)benzenesulfonamide (3.2 g, 68%) as an off-white solid.1H NMR (400 MHz, DMSO-c/6) delta 8.23 (d, J = 8.5 Hz, 2H), 8.04 (d, J = 8.5 Hz, 2H), 7.53 (s, 2H). MS m/z [M-H]”=224.03.

The synthetic route of 4-Cyanobenzenesulphonamide has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; ALEMPARTE-GALLARDO, Carlos; ENCINAS, Lourdes; ESQUIVIAS PROVENCIO, Jorge; (206 pag.)WO2019/34729; (2019); A1;,
Amide – Wikipedia,
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627-12-3, These common heterocyclic compound, 627-12-3, name is Propyl carbamate, 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: CuI (10mol%) and EDA (10mol%) were added to a mixtureof O-alkyl carbamate (1mmol), NaOtBu (1.5mmol) and aryl halide (1mmol) in 2mL toluene and the mixture wasstirred for the appropriate time, which was determined byTLC monitoring, at 100C. After completion of the reaction,the catalyst was removed by filtration and 20mL H2Owas added to the filtrate. The resultant mixture was extractedwith CHCl3.Then the organic phase was washed with water(2 ¡Á 10mL) and dried over anhydrous Na2SO4.After evaporationof CHCl3under reduced pressure, the correspondingcrude product was purified by flash chromatography to givethe desired pure cross-coupling product in good to excellentyield. In the case of using arylboronic acids as couplingpartners, Cu(OAc)2 was employed instead of CuI.

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 627-12-3.

Reference:
Article; Sardarian, Ali Reza; DindarlooInaloo, Iman; Zangiabadi, Milad; Catalysis Letters; vol. 148; 2; (2018); p. 642 – 652;,
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. 630-22-8, name is 2,2-Dimethylpropanethioamide, A new synthetic method of this compound is introduced below., 630-22-8

at room temperature, to dimethylacetamide (35mL) in a (3- (2- (t-butyl) -5- (2-chloro-pyrimidin-4-yl) thiazol-4-yl) -2-fluorophenyl ) allyl carbamate (3.21g, 9.18mmol, 1.0eq.) was added N- succinimide (1.64g, 9.21mmol, 1.0eq.).When LCMS showed complete disappearance of the starting material, 2,2,2-trimethoxy thio acetamide (1.3g, 11.1mmol, 1.2eq.) And the reaction was heated overnight at 60 deg.] C.LCMS showed the reaction was complete.The reaction was poured into water (250mL), and extracted with ethyl acetate content.Extract was dried over sodium sulfate, filtered, and concentrated under reduced pressure.With 20% ethyl acetate / heptane, silica gel chromatography (300g, 3 “diameter column) to give the crude product, in the form of an oil to provide (3- (2- (t-butyl) -5- (2- chloro-pyrimidin-4-yl) thiazol-4-yl) – 2-fluorophenyl) allyl carbamate (2.92g, 70% yield)

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; Pulaixike Company; Zhang, Chao; Ibrahim, Prabha N; Nespi, Marika; Shi, Songyuan; Spevak, Wayne; Habets, Gaston G; Burton, Elizabeth A; Hirth, Klaus-Peter; (181 pag.)CN105228983; (2016); A;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

627-12-3, Adding a certain compound to certain chemical reactions, such as: 627-12-3, name is Propyl 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 627-12-3.

General procedure: CuI (10mol%) and EDA (10mol%) were added to a mixtureof O-alkyl carbamate (1mmol), NaOtBu (1.5mmol) and aryl halide (1mmol) in 2mL toluene and the mixture wasstirred for the appropriate time, which was determined byTLC monitoring, at 100C. After completion of the reaction,the catalyst was removed by filtration and 20mL H2Owas added to the filtrate. The resultant mixture was extractedwith CHCl3.Then the organic phase was washed with water(2 ¡Á 10mL) and dried over anhydrous Na2SO4.After evaporationof CHCl3under reduced pressure, the correspondingcrude product was purified by flash chromatography to givethe desired pure cross-coupling product in good to excellentyield. In the case of using arylboronic acids as couplingpartners, Cu(OAc)2 was employed instead of CuI.

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, Propyl carbamate, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Sardarian, Ali Reza; DindarlooInaloo, Iman; Zangiabadi, Milad; Catalysis Letters; vol. 148; 2; (2018); p. 642 – 652;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

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. 67442-07-3 name is 2-Chloro-N-methoxy-N-methylacetamide, 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. 67442-07-3

4-Iodo-1-(4-methoxybenzyl)-1H-pyrazole (8.1 g, 26 mmol) was dissolved in THF (50 mL) and cooled in an ice bath. Isopropylmagnesium chloride (2.9 M, 8.9 mL, 26 mmol) was added slowly. The reaction mixture was stirred for 10 minutes, and then 2- chloro-N-methoxy-N-methylacetamide (3.5 g, 26 mmol) dissolved in THF (15 mL) was added slowly by syringe. The reaction mixture was warmed to ambient temperature and stirred for 1 hour. The reaction mixture was partitioned between EtOAc and iN HC1, and the organic layer was dried over sodium sulfate, filtered and concentrated to afford crude 2-chloro-1-(l-(4- methoxybenzyl)- 1 H-pyrazol-4-yl)ethanone (7.1 g, 27 mmol, 104 percent yield) as an amber oil that slowly solidified.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Chloro-N-methoxy-N-methylacetamide, and friends who are interested can also refer to it.

Reference:
Patent; ARRAY BIOPHARMA INC.; CELGENE CORPORATION; ALLEN, Shelley; BOYS, Mark Laurence; CHICARELLI, Mark J.; FELL, Jay Bradford; FISCHER, John P.; GAUDINO, John; HICKEN, Erik James; HINKLIN, Ronald Jay; KRASER, Christopher F.; LAIRD, Ellen; ROBINSON, John E.; TANG, Tony P.; BURGESS, Laurence E.; RIEGER, Robert Andrew; PHENEGER, Jed; SATOH, Yoshitaka; LEFTHERIS, Katerina; RAHEJA, Raj K.; BENNETT, Brydon L.; (223 pag.)WO2016/90285; (2016); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

78888-18-3, The chemical industry reduces the impact on the environment during synthesis 78888-18-3, name is tert-Butyl allylcarbamate, I believe this compound will play a more active role in future production and life.

A degassed suspension of Example 294E (2.50 g, 4.51 mmol), Example 314A (2.62 g, 5.87 mmol), and potassium fluoride (0.340 g, 5.87 mmol) in toluene (45 mL) was treated with Pd(PPh3)4 (0.360 g, 0.316 mmol), degassed twice more, and then heated to 115 C. for 14 hours. The suspension was cooled to room temperature and the solvent was removed under reduced pressure. The resulting solid was triturated with ethanol/dichloromethane (10:1) (100 mL) and collected by vacuum filtration provide the desired product (2.3 g, 90%). LCMS (Thermoquest AQA single-quad MS, Genesis C18 column, 3 ?m particle size, 33?4.6 mm; 70% 50 mM ammonium acetate in water to 95% acetonitrile over 6 min, 0.8 to 0.5 mL/min); MS m/e 584.6 (M+H)+, Rt=4.1 minutes; 1H NMR (DMSO-d6, 400 MHz) ? 9.51 (s,1H), 7.99 (d, J=8.0 Hz,1H), 7.95 (s, 1H), 7.70 (d, J=8.0 Hz, 1H), 7.63 (s, 1H), 7.58 (d, J=8.4 Hz, 1H), 7.35 (s, 1H), 7.32 (d, J=8.4 Hz, 1H), 7.21 (d, J=1.5 Hz, 1H), 7.15 (dd, J=7.8 Hz, 7.0 Hz, 1H), 7.08 (dd, J=8.0 Hz, 1.9 Hz, 1H), 6.58 (d, J=16.2 Hz, 1H), 6.21 (td, J=16.2 Hz, J=5.5 Hz, 1H), 5.65 (br s, 1H), 4.04 (s, 3H), 3.91 (s, 3H), 3.80 (br m, 2H), 1.42 (s, 9H).

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

Reference:
Patent; Betschmann, Patrick; Burchat, Andrew; Calderwood, David; Curtin, Michael L.; Davidsen, Steven K.; Davis, Heather M.; Frey, Robin R.; Heyman, Howard R.; Hirst, Gavin; Hrnciar, Peter; Michaelides, Michael; Rafferty, Paul; US2005/20619; (2005); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

3984-14-3,Some common heterocyclic compound, 3984-14-3, name is N,N-Dimethylsulfamide, molecular formula is C2H8N2O2S, 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 6; N’-(3-chloro-5-oxo-5H-pyridor4′,3′:4,51cycloheptarL2-^lpyridine-7-yl)-N,N-dimethylsulfamide (Compound 7); To a stirred solution of 3,7-dichloro-5H-pyrido[4′ ,3′ :4,5]cyclohepta[l,2-&]pyridin-5-one(80 mg, 0.29 mmol) in dioxane (5 mL) were added Pd2(dba)3 (13 mg, 0.014 mmol), 9,9-dimethyl-4,5- bis(diphenylphosphino)xanthene (25 mg, 0.043 mmol), N,N-dimethylsulfamide (36 mg, 0.29 mmol), and Cs2CO3 (0.28 g, 0.87 mmol). The reaction mixture was heated to 95 0C for 2 h, cooled to room temperature, treated with water, and extracted with EtOAc. The combined organics were washed with brine, dried (Na2SO4), concentrated, and purified by flash chromatography to afford the title compound. 1H NMR (600 MHz, CDCl3) delta 8.79 (d, IH); 8.86 (d, 1H);8.76 (s, IH); 8.66 (br s, IH); 8.54 (d, IH); 7.96 (s, IH); 7.38 (d, IH); 7.27 (d, IH); 2.99 (s, 6H). LRMS (ESI) calc’d for (C15H13ClN4O3S) [M+H]+, 365.0; found 365.1.

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

Reference:
Patent; MERCK & CO., INC.; WO2007/50401; (2007); A2;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics