Thionyl Chloride → 3-[3-(Chlorocarbonyl)benzene-1-sulfonyl]triaza-1,2-dien-2-ium-1-ide

Participants

Reaction Conditions

Reaction Steps

11.3 grams (50 milimoles) of 3-(azidosulfonyl) benzoic acid and 31 grams (261 millimoles) of thionyl chloride were added to a 200 ml. round bottom flask equipped with a magnetic stirrer, nitrogen sparge, reflux condenser and heating mantle. The mixture was stirred for 3 hours at 65°C. and then the excess thionyl chloride was stripped under vacuum. A 75 per cent yield of 3-(azido-sulfonyl) benzoyl chloride was obtained and identified by spectroscopic analysis. Said benzoyl chloride was a straw-yellow liquid that slowly crystallized at room temperature and had a melting point of 41°C. and a refractive index of ND24.5 = 1.5751.

Provenance & Evidence