N,1-dimethyl-1H-Imidazole-4-sulfonamide synthesis

Yield:-

Reaction Conditions:

with methylamine in tetrahydrofuran;dichloromethane;water;

Steps:

183.1 N-(4-fluorobenzyl)-8-hydroxy-5-{methyl [(1-methyl-1H-imidazol-4-yl)sulfonyl]amino}-1,6-naphthyridine-7-carboxamide

Step 1: Preparation of N,1-dimethyl-1H-imidazole-4-sulfonamide. To a solution of (1-methyl-1H-imidazol-4-yl)sulfonyl chloride (3.14 g, 17.4 mmol) in methylene chloride was added a solution of methylamine (26 mL of a 2M solution in THF, 52 mmol). The resulting mixture was stirred at room temperature for 16 hr. Water (25 mL) was added and the mixture was extracted with methylene chloride (2*100 mL). The combined organic extracts were washed with water (10 mL) and dried (MgSO₄). The solvent was evaporated in vacuo to afford the title compound. ¹H NMR (CDCl₃, 400 MHz) δ 7.51 (1H, s), 7.49 (1H, s), 4.71 (1H, s), 3.77 (3H, s), 2.70 (3H, m) ppm.

References:

US2003/55071,2003,A1