Indole → HCID 15335320, compound

Participants

Reaction Steps

A solution of 5-chloro-1-methyl-2-(trifluoromethyl)indole (1.79 g, 7.7 mmole) in acetonitrile is cooled to 0° C., treated with chlorosulfonylisocyanate (CSI) (1.0 mL 11.5 mmole) stirred until starting indole cannot be observed by thin layer chromatography, treated with 5 mL of dimethylformamide (DMF), stirred for 0.5 hour and diluted with diethyl ether and water. The phases are separated. The organic phase is washed with water, dried over Na2SO4 and concentrated in vacuo. The resultant residue is chromatographed using silica gel and 4:1 hexanes:ethyl acetate as eluent to give the title product as a white solid, 0.99 g (49.7% yield) mp 166°-167.5° C., identified by IR, 1HNMR, 13CNMR, 19FNMR and mass spectral analyses.

Provenance & Evidence