Category: 88-19-7

Introduction of a new synthetic route about 88-19-7

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.

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. 88-19-7, name is 2-Methylbenzenesulfonamide, A new synthetic method of this compound is introduced below., Formula: C7H9NO2S

{3-[2-methoxy-4-carboxy-benzyl]-1-methyl-1H-indol-5-yl}-carbamic acid cyclopentyl ester (7 kg), dimethyl amino pyridine (2.5 kg), dicyclohexyl carbodiimide (3.9 kg), and dichloromethane (70 L) are charged and stirred for about 15 minutes. O-toluene sulphonamide (3.4 kg) is added at 30 C. and the reaction solution is stirred for about 4 hours at 30 C. The unwanted separated solid is filtered and the reaction solution is washed with dichloromethane (2¡Á12 L). The obtained organic layer is washed with dilute hydrochloric acid and water and separated. The obtained organic solution is distilled off completely under vacuum below 45 C. Acetonitrile (14 L) is added and distilled off completely under vacuum. The obtained crude is cooled to 30 C., acetonitrile (35 L) is added and heated to 85 C., and stirred for about 40 minutes. The resultant reaction solution is cooled to 35 C. and stirred for about 55 minutes. The separated solid is filtered, washed with acetonitrile (7 mL), and suction dried for about 30 minutes. The obtained wet compound is again charged into a reactor containing methanol (84 L), heated to about 60 C., and stirred for about 30 minutes. The reaction solution is cooled to 30 C. and stirred for about 50 minutes for solid separation. The obtained solid is filtered, washed with methanol (7 L), and suction dried for 30 minutes. The solid is dried under vacuum at 70 C. for about 4 hours to afford the title compound.HPLC Purity: 97.5%

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; Anumula, Raghupathi Reddy; Gilla, Goverdhan; Alla, Sampath; Kurella, Sreenivasulu; Kopparapu, Janardana Sarma Ramachandra; Medisetti, Rama Krishna Venkata; Maddula, Srinivasula Reddy; US2009/149662; (2009); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Research on new synthetic routes about 88-19-7

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 of 88-19-7, A common heterocyclic compound, 88-19-7, name is 2-Methylbenzenesulfonamide, molecular formula is C7H9NO2S, 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-[2-Methoxy-4-(toluene-2-sulfonylaminocarbonyl)-benzyl]-1-methyl-1H-indol-5-yl)carbamic acid cyclopentyl ester: Under a nitrogen atmosphere, a mixture of 4-(5-cyclolpentyloxycarbonylamino-1-methyl-1H-indol-3-ylmethyl)-3-methoxy-benzoic acid (800 mg, 1.9 mmol), toluene-2-sulfonamide (341 mg, 2 mmol), 4-(dimethylamino)pyridine (244 mg, 2 mmol), and 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (384 mg, 2 mmol) was dissolved in dichloromethane (30 mL). The mixture was stirred at ambient temperature for about 18 hours, and then poured into 1 M hydrochloric acid (100 mL). Following standard extractive workup with chloroform, the crude product was purified by flash column chromatography on silica gel (petroleum ether/ethyl acetate=2/1, v/v, elution) to afford the title compound (200 mg, 18%). 1H NMR (300 MHz, CDCl3) delta 8.62 (s, 1H), 8.29 (d, 1H, J=8.1 Hz), 7.55-7.22 (m, 9H), 6.81 (s, 1H), 6.50 (s, 1H), 5.23 (s, 1H), 4.08 (s, 2H), 3.91 (s, 3H), 3.75 (s, 3H), 2.71 (s, 3H), 1.96-1.76 (m, 8H); LC-MS: m/z=576 (MH)+; HPLC: 99% (Purity).

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; AUSPEX PHARMACEUTICALS, INC.; US2009/191183; (2009); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics