Chlorosulfonyl isocyanate → HCID 18973105, compound

Participants

Reaction Steps

The title compound was prepared from 3-(2-thenoyl)-4-azaoxindole (Example 4C) according to the procedure of Example 2C, using 3-(2-thenoyl)-5-azaoxindole (500 mg, 2.0 mmol), N-chlorosulfonyl isocyanate (0.26, 3.0 mmol), and acetonitrile (15 mL). Reaction time: 2.25 hours. The crude N-chlorosulfonyl carboxamide was hydrolysed by stirring in DMSO (1.5 mL) for 1.5 hours in a flask open to the air. Ether was added to give a two phase mixture followed by methanol, which gave a homogenous solution. On standing for a brief period, a green precipitate formed which was removed by filtration. The filtrate was allowed to stand overnight, during which time the product crystallized from the solution. This was collected by filtration. Yield: 39 mg (7%). M.p. 250°.

Provenance & Evidence