4-CARBAMOYLMETHOXY-BENZENESULFONYL CHLORIDE synthesis

Yield:69986-21-6 81%

Reaction Conditions:

with chlorosulfonic acid in dichloromethane at 0 - 20;

Steps:

2-{4-(Chlorosulfonyl)phenoxy]acetamide (Intermediate A91)

To a solution of phenoxyacetamide (50 g, 0.333 mol) in dichloromethane (500 mL) was added dropwise chlorosulfonic acid (174.7 g, 1.5 mol) at 0° C. at such a rate to maintain internal temperature between 0 to +5° C. (about 45 min). Some solid formed during this addition. The cooling bath was removed and the reaction mixture was stirred at room temperature overnight. The lower layer in the reaction mixture was added into a vigorously stirring mixture of water (500 mL) and crushed-ice (1500 g). The solid was collected, washed with water (750 mL), and pressed well with a rubber dam. The solid was suspended in acetone (100 mL), stirred for 30 min and collected. After drying, the title compound was isolated as a white solid, weighed 67.3g (81%). ¹H NMR (d⁶-DMSO, 60 MHz) δ 4.5 (s, 3H), 7.1-7.8 (AB, 4H).

References:

US2005/38076,2005,A1 Location in patent:Page/Page column 37