Preparation of 2-(methylthiomethyl)-6-...

Details Preparation of 2-(methylthiomethyl)-6-... Preparation of 2-(methylthiomethyl)-6-...

C - Chemistry, Metallurgy

07

C

260/601.2

C07C 149/273 (1985.01)

Patent

CA 1218078

PREPARATION OF 2-(METHYLTHIOMETHYL)-6-(TRIFLUOROMETHYL) ANILINE FROM ORTHO-AMINOBENZOTRIFLUORIDE ABSTRACT This invention relates to a process for the preparation of 2-(methylthiomethyl)-6-(trifluoromethyl) aniline, [MTA], from ortho- aminobenzotrifluoride, (OABT), employing a single solvent transformation via a sulfilimine intermediate. A sulfilimine hydrochloride salt is pre- pared by the oxidative addition of dimethyl sulfide to OABT in the presence of N-chlorosuccinimide. Neutralization of the sulfilimine hydrochloride salt with aqueous sodium hydroxide followed by phase separation results in an organic phase containing free sulfilimine and an aqueous phase generally containing succinimide and/or sodium succinimide. In a preferred embodiment the phase separation is per- formed in such a manner to leave a catalytic amount of succinimide in the organic phase. The free sulfilimine catalytically rearranges at moderate temperatures in the presence of this succinimide catalyst to form MTA. The aqueous phase separated after neutralization of the sulfilimine hydrochloride salt contains succinimide and/or sodium succinimide which may be converted by the action of chlorine to N-chlorosuccinimide which in turn may be recycled to the first step in the process.

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