Anomalous Reactions in Attempts to Prepare 3-Alkylthioindoles

Abstract

Indole magnesium bromide reacting with ethanesulfenyl chloride produces ethyl ~llercaptan, diethyl disulfide, indole, 3-ethylindole, 3-ethylthioindole, and 3,3'-diindolyl sulfide, along with a t least three compounds not yet identified.T h e reaction of ethyl mercaptan with N-benzoyl-3-bromoindole in dimethylformamide containing potassi~~m carbonate produces indole, 3-bromoindole, ethyl thiolobenzoate, 3-ethylindole, diethyl disulfide, and 3-ethylthioindole.