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. 636-76-0, name is 3-Sulfamoylbenzoic acid belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Application In Synthesis of 3-Sulfamoylbenzoic acid
To 3-aminosulfonylbenzoic acid (4.0g), N,N-dimethylformamide (53 ml), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (3.8 g), 1-hydroxybenzotriazole (2.7 g), N,O-dimethylhydroxylamine hydrochloride (1.9 g), and triethylamine (2.8 ml) were added under ice cooling and the mixture was stirred at room temperature for 12 hours. A potassium hydrogensulfate aqueous solution and ethyl acetate were added to the reaction solution and the mixture was separated. The aqueous layer was extracted with ethyl acetate. The combined organic layer was successively washed with distilled water, saturated sodium hydrogencarbonate aqueous solution, and saturated saline, dried over with anhydrous sodium sulfate, then concentrated. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/2). To the obtained N-methoxy-N-methyl-3-aminosulfonylbenzamide (1.8 g), tetrahydrofuran (36 ml) and ethyl magnesium bromide (0.89M tetrahydrofuran solution, 41 ml) were added under ice cooling, the mixture was stirred at room temperature for 3 hours, then saturated ammonium chloride aqueous solution and ethyl acetate were added to reaction solution, the mixture was separated, then organic layer was successively washed with saturated saline, dried over with anhydrous sodium sulfate, then concentrated. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/1). To the obtained 3-propionylbenzenesulfonamide (0.97 g), ethanol (2.5 ml), sodium acetate (0.56 g), and hydroxylamine hydrochloride (0.35 g) were added and the mixture was stirred at 90C for 3 hours. Ethyl acetate and water were added to the reaction solution, the mixture was separated, then the organic layer was successively washed with saturated saline, dried over with anhydrous sodium sulfate, then concentrated. The obtained 3-(N-hydroxypropanimidoyl)benzenesulfonamide was used instead of the starting material compound of Reference Example 109, that is, 1-(4-aminophenyl)propan-1-on oxime, for the similar procedure as with Reference Example 109 to obtain the title compound. NMR (DMSO-d6): delta8.50-8.36(3H, br), 7.92(1H, s), 7.83(1H, d, J=7.5Hz), 7.71-7.60(2H, m), 7.42(2H, s), 4.33-4.21(1H, br), 2.00-1.70(2H, m), 0.75(3H, t, J=7.4Hz) MS: 215(M+H)+
The synthetic route of 636-76-0 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; Asubio Pharma Co., Ltd.; Daiichi Sankyo Company, Limited; EP2025672; (2009); A1;,
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