(Chlorothio)formyl chloride → 2H-1,3,4-Oxathiazol-2-one

Participants

Reaction Steps

To a suspension of 1-(tetrahydropyran-4-yl)methyl-7-chloro-1H-indole-3-carboxylic acid amide (8.0 g, 27.0 mmol) in tetrahydrofuran (100 ml) was added chlorocarbonylsulfenyl chloride (4.7 ml, 55.0 mmol) and the reaction mixture was heated at reflux for 3 h and allowed to cool. The precipitate was filtered off and dried to give 5-(1-tetrahydropyran-4-yl) methyl-7-chloro-1H-indole)-[1,3,4]-oxathiazol-2-one (5.3 g, 15.0 mmol) as a white solid. The filtrate was concentrated in vacuo, and the resulting solid was washed with 5% ethylacetate in n-heptane then dried to leave 7-chloro-3-([1,3,4]-oxathiazol-2-on-5-yl)-1-(tetrahydropyran-4-yl)methyl-1H-indole (2.6 g, 7.0 mmol) as a pink solid.

Provenance & Evidence