Monsanto Company

Audrey Y Ku

John P Chupp

Terry M Balthazor

Thomas E Neumann

Thomas E Nickson

This invention pertains to two substituted benzotrifluoride compounds useful as chemical intermediates for a new class of 2-haloacetanilide herbicides and a process for making these intermediates. The process generally involves nitration and reduction of the corresponding benzotrifluoride compound.

Substituted benzotrifluoride compounds as chemical intermediates and a

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 prepared 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 performed 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.

Preparation of 2-(methylthiomethyl)-6-(trifluoromethyl)aniline from

This invention relates to a process for preparing ortho-(alkylthiomethyl) anilines by catalytic rearrangement of aromatic sulfilimines in an inert organic solvent. The sulfilimine can be prepared using any of the procedures available in the art. This invention particularly relates to a new class of sulfilimine rearrangement catalysts.

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Chesterfield, MO, United States of America

Audrey Y Ku