Category: amides-buliding-blocks

Electric Literature of 17641-08-6, In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 17641-08-6 as follows.

General procedure: A mixture of the key intermediate 13 (1.0 mmol), diverse 2-chloro-N-sbustituted acetamidederivatives 15 (1.0 mmol) and potassium carbonate (K2CO3) (0.15 g, 1.1 mmol) in 5.0 mL ofanhydrous ethanol was stirred and refluxed for 2.0-2.5 h. After the reaction was complete accordingto the TLC detection, the precipitate was filtered off and solvent was removed under reducedpressure and the residue was purified by column chromatography to give the target compounds inyields of 57-78%.

According to the analysis of related databases, 17641-08-6, the application of this compound in the production field has become more and more popular.

Reference:
Article; Zhao, Pei-Liang; Chen, Peng; Li, Qiu; Hu, Meng-Jin; Diao, Peng-Cheng; Pan, En-Shan; You, Wen-Wei; Bioorganic and Medicinal Chemistry Letters; vol. 26; 15; (2016); p. 3679 – 3683;,
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Reference of 6292-59-7,Some common heterocyclic compound, 6292-59-7, name is 4-(tert-Butyl)benzenesulfonamide, molecular formula is C10H15NO2S, 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: 2.2 General procedure: 4-methyl-N-phenylbenzenesulfonamide (3a) A 25 mL oven-dried reaction vessel was charged with Pd(TFA)2 (2.3 mg, 0.01 mmol), 1,10-phenanthroline (3.6 mg, 0.02 mmol), p-toluene sulfonamide (1a, 34.2 mg, 0.2 mmol), cyclohexanone (2a, 32 muL, 0.3 mmol). The reaction vessel was flushed with oxygen three times and then sealed. Toluene (0.7 mL) was added by syringe and the resulting solution was stirred at 140 ¡ãC for 40 h. After cooling to room temperature, the volatiles were removed under vacuum and the residue was purified by column chromatography (silica gel, petroleum ether/ethyl acetate = 4:1) to give the corresponding product 3a (39.9 mg) as white solid in 81percent yield.

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

Reference:
Article; Cao, Xiangxiang; Bai, Yang; Xie, Yanjun; Deng, Guo-Jun; Journal of Molecular Catalysis A: Chemical; vol. 383-384; (2014); p. 94 – 100;,
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Application of 123664-84-6, In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 123664-84-6 as follows.

(1) In 100 ml of anhydrous methylene chloride were dissolved 10 g of 3-methylsulfonylamino-4-phenoxyanisole and 2.81 g of acetyl chloride. Thereto was added 9.1 g of aluminum chloride in 5 minutes with ice-cooling. The mixture was stirred for 1 hour at 20-25 C. The reaction mixture was introduced into 100 ml of ice water. The resulting organic layer was separated, washed with water and a saturated aqueous sodium chloride solution in this order, and dried with anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure. The residue was recrystallized from isopropyl alcohol to obtain 9.83 g (yield: 86%) of methyl 4-methylsulfonylamino-2-methoxy-5-phenoxyphenyl ketone having a melting point of 108.5-110 C. IR (KBr) cm-1: 3300, 1640, 1600, 1490, 1330, 1210, 1155

According to the analysis of related databases, 123664-84-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Toyama Chemical Company, Ltd.; US4954518; (1990); A;,
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Reference of 35303-76-5, The chemical industry reduces the impact on the environment during synthesis 35303-76-5, name is 4-(2-Aminoethyl)benzenesulfonamide, I believe this compound will play a more active role in future production and life.

A THF solution (20 ml) of 4- (4-isocyanatobutyl) benzene (1.71 mmol) and 4- (2-aminoethyl) benzenesulfonamide (20 ml) was stirred at 40-45 ¡ã C for 24 hours. The next day, the completion of the reaction was confirmed by TLC. The solvent was distilled off and ammonium chloride (100 ml), water (50 ml) and ethyl acetate (100 ml) were added to the remaining residue. The organic layer was treated with brine and dried over sodium sulfate. The solvent was distilled off and the resulting concentrate was adsorbed onto silica gel using methylene chloride. The mixture was purified by column chromatography using ethyl acetate in hexane to give the title compound.

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-(2-Aminoethyl)benzenesulfonamide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; The Industry & Academic Cooperation in Chungnam National University (IAC); Jung, Sang-Hun; Woo, Sun-Hee; Kim, Sang- Kyum; Jeon, Eun-Seok; Lee, Yu-Jung; Meunikam, Manoj; Jalani, Hiteshkumar; Sharma, Niti; (205 pag.)KR2016/108281; (2016); A;,
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Synthetic Route of 16982-21-1, A common heterocyclic compound, 16982-21-1, name is Ethyl 2-amino-2-thioxoacetate, molecular formula is C4H7NO2S, 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.

4B. Ethyl 4-phenylthiazole-2-carboxylate A mixture of 2-bromo-1-phenylethanone (1.790 g, 8.99 mmol) and ethyl 2-amino-2-thioxoacetate (Example 4A, 1.20 g, 9.01 mmol) in benzene (80 mL) and ethanol (10 mL) was stirred at room temperature for 18 h. The mixture was heated at 80 C. for 1 h. The solvent was evaporated under reduced pressure and the residue was partitioned between ethyl acetate (300 mL) and saturated aqueous sodium bicarbonate (100 mL). The organic phase was washed with brine, dried over anhydrous magnesium sulfate and concentrated in vacuo. The residual clear oil was chromatographed on silica gel (4*10 cm, elution toluene-ethyl acetate 0-2-4%) and gave a yellow oil (1.588 g). This was distilled in vacuo (bp: 105-115 C./0.1 torr, bulb to bulb distillation, air bath temperature) to provide the title material (1.409 g, 67%) as a pale yellow syrup which solidified to an almost colorless solid upon standing. LC (Method C): 2.009 min. HRMS (ESI) calcd for C12H12NO2S [M+H]+ m/z 234.0583. found 234.0597. 1H NMR (CDCl3, 400 MHz) delta ppm: 1.48 (t, J=7.2 Hz, 3H), 4.52 (q, J=7.2 Hz, 2H), 7.35-7.49 (m, 3H), 7.75 (s, 1H), 7.93-8.00 (m, 2H).

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; Kornacker, Michael G.; Mapelli, Claudio; Riexinger, Douglas James; US2013/289238; (2013); A1;,
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Synthetic Route of 1746-77-6,Some common heterocyclic compound, 1746-77-6, name is Isopropyl carbamate, 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.

Isopropyl carbamate (30 g, 291 mmol, available from TCI) was charged to a 3 L Lara vessel and dry Tetrahydrofuran (THF) (150 ml) added. (2E)-2-butenoyl chloride (31.2 ml, 326 mmol, available from Aldrich) was added under nitrogen and the jacket cooled to -30 C. When the solution temperature reached -17 C. 1M Lithium tert-butoxide (655 ml, 655 mmol) was added by peristaltic pump over 2 hours, keeping the reaction temperature between -10 C. and -18 C. Once the addition was complete the mixture was complete the mixture was stirred for 30 mins and brought to 0 C. Diethyl ether (450 ml) and 1M HCl (375 ml) were added and the mixture brought to 20 C. with vigorous stirring. The stirring was stopped, the layers allowed to separate and the aqueous layer run off. Brine (375 ml) was added and the mixture stirred vigorously. The stirring was stopped, the layers allowed to separate and the aqueous layer run off. The organic layer was dried (magnesium sulfate), filtered and evaporated to a brown oil (60 g). The mixture was loaded on to a 40+M Biotage silica column and eluted with DCM:ethyl acetate (1:1 to 0:1, 10 CV). The product containing fractions were evaporated to dryness and loaded on to a 1500 g Redisep Isco silica column and eluted with a gradient of 0 to 40% ethyl acetate in cyclohexane. The clean, product containing fractions were evaporated to an off white solid (15.41 g). LCMS (Method C): Rt=0.68, MH+=172

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

Reference:
Patent; Demont, Emmanuel Hubert; Garton, Neil Stuart; Gosmini, Romain Luc Marie; Hayhow, Thomas George Christopher; Seal, Jonathan; Wilson, David Matthew; Woodrow, Michael David; US2012/208798; (2012); A1;,
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Some common heterocyclic compound, 153248-46-5, name is [1-[(Boc-amino)methyl]cyclopropyl]methanol, molecular formula is C10H19NO3, 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: C10H19NO3

To a solution of PPh3 (244 mg, 0.90 mmol) in anhydrous tetrahydrofuran (10 mL) was added DIAD (188 mg, 0.90 mmol) by syringe at 05 C, followed by a solution of tert-butyl (1 -(hydroxymethyl)cyclopropyl)methylcarbamate (110-13) (178 mg, 0.90 mmol) in anhydrous tetrahydrofuran (5 mL). The resulting mixture was poured into a solution of compound 308-7 (100 mg, 0.30 mmol) in anhydrous tetrahydrofuran (5 mL) at ambient temperature and stirred for 10 mm. The reaction mixture was quenched with water and extracted with ethyl acetate. The organic layer was washed with water and brine, dried over anhydrous sodium sulfate and evaporated in vacuo. The crude product was purified by column chromatography (dichloromethane/ethyl acetate: 5/1) to afford the title compound 309-17 as a yellow solid (100 mg, crude). LCMS: 522.3 [M+1] .

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 153248-46-5, its application will become more common.

Reference:
Patent; PHARMAENGINE, INC.; CAI, Xiong; QIAN, Changgeng; WANG, Yanong Daniel; (98 pag.)WO2017/132928; (2017); A1;,
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Synthetic Route of 636-76-0, These common heterocyclic compound, 636-76-0, name is 3-Sulfamoylbenzoic acid, 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.

3-sulfamoylbenzoic acid (150mg, 0.746 mmol) was refluxed in the presence of concentrated Sulfuric acid (4.82 mg, 0.037 mmol) in methanol (5 ml_) at 70 C for overnight. Reaction was monitored by TLC. After completion of the reaction, Solvent was removed by vacuum and then compound was purified by flash chromatography afforded the methyl 3-sulfamoylbenzoate (1 15 mg, 0.524 mmol, 70.2 % yield) as a solid. 1 H NMR (CDCI3, 400 MHz): delta 8.53 (m, 1 H), 8.18 (d, 1 H, J = 8.0 Hz), 8.08 (d, 1 H, J = 7.6 Hz), 7.57 (t, 1 H, J = 8.0 Hz), 3.92 (s, 3H). Mass [M+H]+ :216.0

Statistics shows that 3-Sulfamoylbenzoic acid is playing an increasingly important role. we look forward to future research findings about 636-76-0.

Reference:
Patent; UNIVERSITY OF UTAH RESEARCH FOUNDATION; VANKAYALAPATI, Hariprasad; SORNA, Venkataswamy; WARNER, Steve, L.; BEARSS, David, J.; SHARMA, Sunil; STEPHENS, Bret; WO2013/25805; (2013); A1;,
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Related Products of 50667-69-1, A common heterocyclic compound, 50667-69-1, name is 2,2,2-Trifluoro-N-(hydroxymethyl)acetamide, molecular formula is C3H4F3NO2, 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.

To a solution of l-chloro-2-nitrobenzene (10.0 g, 0.063 mmol) in cone, sulphuric acid (150 mL) was added N-hydroxy methyl trifluoro acetamide (9.98 g, 0.069 mmol). The reaction mixture was heated at 70-80C for 24 h. The reaction mass was quenched in ice cold water, neutralised with sodium hydroxide and extracted with DCM. The organic layer was concentrated and the obtained crude product was purified by column chromatography on silica gel eluting with 4% EtOAc: pet. ether to afford 5.5 g of desired product. 1H NMR (300 MHz, DMSO d6): 4.48 (d, J = 3.9 Hz, 2H), 7.62- 7.64 (m, 1H), 7.72- 7.78 (m, 1H), 7.97- 8.01 (m, 1H), 10.09 (brs, 1H) .

The synthetic route of 50667-69-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLENMARK PHARMACEUTICALS S.A.; GHARAT, Laxmikant Atmaram; MUTHUKAMAN, Nagarajan; KHAIRATKAR-JOSHI, Neelima; KATTIGE, Vidya Ganapati; WO2013/186692; (2013); A1;,
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Amide – an overview | ScienceDirect Topics

108-13-4, name is Malonamide, 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. Formula: C3H6N2O2

To a solution of malonic-acid diamide (1 g) in DMF (15 mL), N,N dimethylformamide-dimethylacetal (1.4 g) added slowly. Then the mixture heated up to 50 C. and stirred for 3 h. The product isolated after concentration the mixture followed by crystallization (410 mg).1H NMR. (DMSO d6) delta: 7.45 and 7.02 (each bs, 4H, 2¡Á-NH2), 7.40 (s, 1H, -CH), 2.94 and 2.89 (2¡Ás, each 3H, 2¡Á-NCH3).13C NMR (DMSO d6) delta: 169.16 and 169.15 (2¡ÁCO), 151.08 (-HN-CH), 96.37 (C qvat.), 43.07 and 42.95 (2¡ÁNCH3).

The synthetic route of 108-13-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Dekany, Gyula; Agoston, Karoly; Bajza, Istvan; B¡ãjstrup, Marie; Kroeger, Lars; US2009/234111; (2009); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics