Triethylamine → Chlorosulfamic acid

Participants

Reaction Conditions

Reaction Steps

Sulfamoyl chloride was prepared in situ by cautiously adding to a solution of chlorosulfonyl isocyanate (7.05 g, 0.05 mol) in acetonitrile (50 ml) cooled to 0-5° C., water (0.9 ml) in acetonitrile (5 ml) keeping the temperature below 10° C., whilst stirring for 1 hour. A solution of 1-(prop-2-en-1-yl) aniline (6.65 g, 0.05 mol) and triethylamine (5.05 g, 0.05 mol) was stirred at 0-5° C. and the sulfamoyl chloride prepared above was added slowly keeping the temperature below 10° C., stirring overnight. The reaction was poured into ice-water(100 ml) and the product, 1-phenyl-1-(prop-2-en-1-yl) sulfamide was collected by filtration. This was treated with 2-methylpropionaldehyde and methane sulfonic acid as described previously to give 3,4-dihydro-4-(2-methylethyl)-1-(prop-2-en-1-yl)-1H-2,1,3-benzothiadiazine-2,2-dioxide. This compound was converted to 3,4-dihydro-4-(2-methylethyl)-1-(2-oxoethyl)-1H-2,1,3-benzothiadiazine-2,2-dioxide by methods discussed previously.

Provenance & Evidence