Category: amides-buliding-blocks

These common heterocyclic compound, 174799-52-1, name is tert-Butyl (2-(benzylamino)ethyl)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. name: tert-Butyl (2-(benzylamino)ethyl)carbamate

Preparation 64: Synthesis of tert-butyl 2-(N-benzyl-N-methylamino)ethylcarbamate (B)To a cooled (~5 C) solution of compound A (6.2 g, 25.0 mmol) and TEA (3.0 g, 29.7 mmol, 4.13 mL) in chloroform (50 mL) was added iodomethane (4.2 g, 29.7 mmol, 1.85 mL). The pressure tube was sealed, and the mixture stirred at ambient temperature for 20 h. The mixture was then precipitated with ether (300 mL); the white solid was filtered off and washed with ether (50 mL). The filtrate was concentrated and the residual yellow oil (5.2 g) was purified by silica gel column chromatography (2-10% MeOH gradient in DCM) to give compound B (3.3 g, 12.5 mmol, 50%) as a colorless oil. TLC Rf (DCM/MeOH 9:1): 0.55. LC-MS [M+H] 264.3 (C15H24N2O2 +H, calc: 264.4).

The synthetic route of tert-Butyl (2-(benzylamino)ethyl)carbamate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PHARMACOFORE, INC.; JENKINS, Thomas, E.; HUSFELD, Craig, O.; SEROOGY, Julie, D.; WRAY, Jonathan, W.; WO2011/133150; (2011); A1;,
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Related Products of 216961-61-4, The chemical industry reduces the impact on the environment during synthesis 216961-61-4, name is tert-Butyl (10-aminodecyl)carbamate, I believe this compound will play a more active role in future production and life.

General procedure 2. Starting compound III: S-Methyl N-cyano-N’-(2-methyl4-pyridylisothiourea. Starting compound IV: 10-t-Butoxycarbonylaminodecylamine. Purification: Flash chromatography (Eluent 1% NH3(aq) and 0-10% MeOH in CH2Cl2). The compound was obtained as a yellow oil. 13C NMR (CDCl3) delta: 158.1, 157.3, 155.5, 149.4, 146.2, 116.5, 113.5, 112.0, 77.2, 41.7, 29.4, 28.9, 28.8, 28.6, 28.6, 28.6, 28.2, 26.2, 26.1, 24.0.

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, tert-Butyl (10-aminodecyl)carbamate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Leo Pharmaceutical Products, Ltd. A/S; US6346520; (2002); B1;,
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Reference of 4141-08-6, 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. 4141-08-6 name is 2-Amino-N-methylbenzamide, 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.

To a solution of 2-amino-N-methylbenzamide 15.00g(0.1mol) and triethylamine 12.10g(0.12mol) in 150 mL dichloromethane was added 12.40g(0.11mol) chloroacetyl chloride in 30mL dichloromethane at room temperature for 0.5 hours. Then the reaction mixture was continued stirring at room temperature for another 2-3 hours and monitored by TLC. After the reaction was over, the mixture was concentrated under reduced pressure, the residual was filtered and washed with 50ml of 10% diluted hydrochloric acid, 50ml of saturated sodium bicarbonate solution, 50ml of water and 50ml of petroleum ether successively, then dried to give 18.90g intermediate 2-(2-chloroacetamido)-N-methylbenzamide as white solid with yield of 83.4%, m.p. 155-157C.

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

Reference:
Patent; Sinochem Corporation; Shenyang Research Institute of Chemical Industry Co., Ltd.; REN, Lanhui; LIU, Changling; WANG, Lizeng; LI, Zhinian; SUN, Xufeng; LAN, Jie; WU, Qiang; CHI, Huiwei; EP2636669; (2013); A1;,
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Adding a certain compound to certain chemical reactions, such as: 63920-73-0, name is 2-Amino-4,6-dimethoxybenzamide, 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 63920-73-0, Product Details of 63920-73-0

Example 26. Preparation of 2-[4-(5,7-Dimethoxy-4-oxo-3,4-dihydro-quinazolin-2-yl)-2,6-dimethyl-phenoxy]-N-(4-methoxy-phenyl)-acetamide [0257] To a solution of 4-hydroxy-3,5-dimethyl-benzaldehyde (9.00 g, 60.0 mmol) in ethanol (300 mL) were added potassium carbonate (24.9 g, 180 mmol) and methyl bromoacetate (11.4 mL, 120 mmol). The reaction mixture was stirred at 95C under nitrogen for 16 hours. The mixture was concentrated to dryness under reduced pressure. Water (150 mL) and 1 N NaOH solution (90 mL) were added to the residue. The mixture was stirred at room temperature for 30 minutes, then washed with ether. Concentrated HCI was added slowly to the aqueous solution until a large amount of white precipitate formed. The solid was filtered, washed with water, and air-dried, to give (4-formyl-2,6-dimethyl-phenoxy)- acetic acid as a white solid. Yield: 11.1 g (89%).[0258] To a solution of (4-formyl-2,6-dimethyl-phenoxy)-acetic acid (3.12 g, 15.0 mmol) and 2-amino-4,6-dimethoxy-benzamide (2.94 g, 15.0 mmol) in N,N-dimethylacetamide (50 mL) were added sodium hydrogen sulfite (58.5 wt%, 3.02 g, 16.5 mmol) and p-toluenesulfonic acid monohydrate (0.285 g, 1.50 mmol). The reaction mixture was stirred at 1200C for 17 hours under nitrogen and cooled to room temperature. The precipitate was filtered, washed with water, then methanol, and air-dried to give 1.29 g [4-(5,7-dimethoxy-4-oxo-3,4-dihydro-quinazolin-2-yl)-2,6-dimethyl-phenoxy]-acetic acid. The filtrate was concentrated to dryness and water was added. The suspension was stirred for 30 minutes and filtered. The solid was washed with water, then methanol. After air drying, 3.78 g more [4-(5,7-dimethoxy-4-oxo-3, 4-dihydro-quinazolin-2-yl)-2,6-dimethyl-phenoxy]- acetic acid was obtained. Yield: 5.07 g (88%).[0259] To a mixture of [4-(5,7-dimethoxy-4-oxo-3,4-dihydro-quinazolin-2-yl)-2,6-dimethyl-phenoxy]-acetic acid (0.400 g, 1.04 mmol), 1-ethyl-3-(3′-dimethylaminopropyl)carbodiimide hydrochloride (EDCI; 0.240 g, 1.24 mmol), 1-hydroxybenzotriazole hydrate (HOBt; 0.17 g, 1.24 mmol) in DMF (10 ml_) was added 4-methylmorpholine (0.20 mL, 1.8 mmol). After 10 minutes, p-anisidine (0.26 g, 2.08 mmol) was added. The mixture was stirred at room temperature under nitrogen for 2.5 days. The solvent was removed under reduced pressure. Water was added, stirred for 30 minutes. The solid was filtered, washed with water, and dried in air. The crude product was purified by column chromatography (silica gel, 230-400 mesh; 5% MeOH in CH2CI2 as eluent). The product fractions were combined, concentrated to dryness. The solid was dissolved in small amount of dichloromethane, precipitate out by adding ether. The precipitate was filtered, washed with ether, dried under vacuum to afford the title compound as a white solid. Yield: 0.26 g (51%). 1H NMR (400 MHz, CDCI3): delta 10.30 (br s, 1 H), 8.52 (s, 1 H), 7.83 (s, 2H), 7.58 (dd, J = 6.8 and 2.0 Hz, 2H), 6.93 (dd, J = 6.8 and 2.0 Hz, 2H), 6.84 (d, J = 2.4 Hz, 1 H), 6.48 (d, J = 2.0 Hz, 1 H), 4.44 (s, 2H), 3.97 (s, 3H), 3.94 (s, 3H), 3.83 (s, 3H), 2.42 (s, 3H). MS (ES+) m/z: 490.55 (M+1).

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; RESVERLOGIX CORP.; HANSEN, Henrik, C.; WAGNER, Gregory, S.; ATTWELL, Sarah, C.; MCLURE, Kevin, G.; KULIKOWSKI, Ewelina, B.; WO2010/123975; (2010); A1;,
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54468-86-9, name is 2-Amino-N,N-dimethylbenzenesulfonamide, belongs to amides-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Application In Synthesis of 2-Amino-N,N-dimethylbenzenesulfonamide

To a screw cap vial was added 2-amino-(N, N-dimethyl) phenylsulphonamide (34.9mg, 0. [17MMOL),] DPT (40.5mg, 0. [17MMOL)] and [CH2CI2] (3mL). The resultant bright orange solution was stirred at room temperature for 1 hour and forty-five minutes. At this time, DPT was again added (21. Omg, 0. [09MMOL)] and after one hour of stirring, a TLC was taken showing the reaction to be 50% complete. DPT was again added (21. Omg, 0. [09MMOL)] and the reaction was heated to [50C] for one hour. The reaction mixture was put through an SPE tube [(CH2CI2)] to yield the title compound as a yellow oil (34. [1 MG,] 98%).

The synthetic route of 54468-86-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NPS ALLELIX CORP.; WO2004/22534; (2004); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

These common heterocyclic compound, 18469-37-9, name is 4-Bromo-N,N-dimethylbenzamide, 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. Computed Properties of C9H10BrNO

Example 23 Reduction of N,N-dimethyl-4-bromobenzamide A 20-mL eggplant flask equipped with a three-way cock and a magnetic stirrer was heat dried while pumping to a vacuum of 5 Pa before its interior was purged with argon atmosphere. Into the flask, iron complex A (1.0 mg, 0.002 mmol) was admitted as catalyst and dissolved in toluene (0.5 mL). To the solution, 1,2-bis(dimethylsilyl)benzene (475 muL) was added through a syringe, and N,N-dimethyl-4-bromobenzamide (228 mg, 1.0 mmol) was added. The solution was stirred at 100 C. for 30 minutes. Toluene was distilled off in vacuum. The crude product was purified by silica gel-packed column chromatography using hexane/ethyl acetate (20/1) as developing solvent, obtaining N,N-dimethyl-4-bromobenzylamine (184 mg, 0.86 mmol, 86%).

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

Reference:
Patent; Shin-Etsu Chemical Co., Ltd.; Kyushu University, National University Corporation; NAGASHIMA, Hideo; SUNADA, Yusuke; TSUTSUMI, Hironori; HASHIMOTO, Toru; SAKUTA, Koji; (24 pag.)US2016/23196; (2016); A1;,
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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. 37394-93-7, name is 2-Chloro-N-(o-tolyl)acetamide, A new synthetic method of this compound is introduced below., name: 2-Chloro-N-(o-tolyl)acetamide

General procedure: General procedure.A mixture of 4 (4.59 g, 0.01 mol) and 2-chloro-N-substitutedacetamide derivatives (0.01 mol) in dry acetone (30 mL) andanhydrous K2CO3 (1.38 g, 0.01 mol) was stirred at room temperaturefor 8 h, filtered and the solid product formed was crystallizedfrom ethanol to give 5-18.

The synthetic route of 37394-93-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Bua, Silvia; Ghorab, Mostafa M.; Soliman, Aiten M.; Supuran, Claudiu T.; European Journal of Medicinal Chemistry; vol. 200; (2020);,
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Synthetic Route of 70-55-3, The chemical industry reduces the impact on the environment during synthesis 70-55-3, name is 4-Methylbenzenesulfonamide, I believe this compound will play a more active role in future production and life.

A solution of 4-(bromomethyl) owing procedure. 4-Methylbenzenesulfonamide (0.5 g, 2.92 mmol) was dissolved in chloroform (10 mL) and N-bromosuccinimide (0.546 g, 3.07 mmol) and benzoyl peroxide (0.035 g, 0.146 mmol) were added and the reaction was heated overnight at 63 °C. The succinimide crystallized out at room temperature to afford a crude solution of 4- (bromomethyl)benzenesulfonamide.

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

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; ADAMS, Nicholas David; BENOWITZ, Andrew B.; RUEDA BENEDE, Maria Lourdes; EVANS, Karen Anderson; FOSBENNER, David T.; KING, Bryan Wayne; LI, Mei; MILLER, William Henry; REIF, Alexander Joseph; ROMERIL, Stuart Paul; SCHMIDT, Stanley J.; WIGGALL, Kenneth; (1283 pag.)WO2017/216726; (2017); A1;,
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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. 123986-64-1, name is tert-Butyl 4-(hydroxymethyl)benzylcarbamate, A new synthetic method of this compound is introduced below., Recommanded Product: tert-Butyl 4-(hydroxymethyl)benzylcarbamate

Dess-Martin periodinane (1.25 eq) was added to a flask with a stir bar. Diluted with DCM (0.25 M), and the resulting slurry was stirred vigorously at roomtemperature. Added a solution of alcohol (1.00 eq) in DCM (0.20 M) in dropwise fashion, and the resulting reaction mixture was stirred vigorously under Ar at room temperature. After 2.5 hrs, TLC indicated complete conversion of starting material. The reaction mixture was poured over a 1:1 mixture of saturated aqueous NaHCO3 and saturated aqueous Na2S2O3 (55 mL per mmol alcohol). The resulting organic layer was dried over anhydrous sodium sulfate, filtered, and evaporated under reduced pressure. A solution ofamine (1.00 eq) in DCM (0.12 M) was added to a flask with a stir bar. Added a solution of aldehyde (1.05 eq) in DCM (0.53 M), and the resulting mixture was stirred under Ar at room temperature for 5 mm. After this time, acetic acid (1.00 eq) was added, and the resulting mixture was stirred under Ar at room temperature for 15 mm. After this time, sodium triacetoxyborohydride (3.00 eq) was added, and the resulting reaction mixture was allowed to stir overnight at room temperature under Ar. In the morning, thereaction mixture was diluted with DCM and washed once with 1 M aqueous sodium hydroxide. The resulting aqueous layer was extracted 3 times with DCM. Combined organic layers were dried over anhydrous sodium sulfate, filtered, and evaporated under reduced pressure. The cmde material was taken up in DCM (40 mL per mmol amine), filtered, and evaporated under reduced pressure.

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; EMORY UNIVERSITY; LIOTTA, Dennis C.; JECS, Edgars; WILSON, Robert James; NGUYEN, Huy Hoang; KIM, Michelle Bora; WILSON, Lawrence; MILLER, Eric James; TAHIROVIC, Yesim Altas; TRUAX, Valarie; KAISER, Thomas; (311 pag.)WO2018/156595; (2018); A1;,
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Synthetic Route of 2618-96-4, 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. 2618-96-4, name is Dibenzenesulfonimide belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: Under N2, ynamide 1a (0.300 mmol, 108.7 mg) and diphenylsulfonimide (2a; 0.600 mmol, 178.4 mg, 2.00 equiv) were dissolved in CH2Cl2 (4.00 mL). The reaction mixture was allowed to stir at r.t. After the consumption of 1a (4.5 h, TLC, eluent: PE-EtOAc, 4:1), the mixture was concentrated, and the residue was purified by flash chromatography on silica gel (eluent: PE-EtOAc, 6:1 ? 4:1) to afford 3a.

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

Reference:
Article; Yu, Lian; Deng, Yuan; Cao, Jian; Synthesis; vol. 47; 6; (2015); p. 783 – 788;,
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