Preparation of ortho-(alkylthiomethyl) anilines by catalytic sulfilimine rearrangement.

摘要

This invention relates to a process for preparing ortho-(alkylthiomethyl)anilines, e.g. 2-(methylthiomethyl)-6-(trifluoromethyl)aniline of the formula
<Chemistry id="chema01" num="0001"><Image id="ia01" he="21" wi="41" file="IMGA0001.TIF" imgContent="chem" imgFormat="TIFF" inline="no" /></Chemistry>by catalytic rearrangement of aromatic sulfimides, e.g. N-(2-trifluoromethylphenyl)-S,S-dimethylsulfimide of the formula
<Chemistry id="chema02" num="0002"><Image id="ia02" he="23" wi="44" file="IMGA0002.TIF" imgContent="chem" imgFormat="TIFF" inline="no" /></Chemistry>in an inert organic solvent. The sulfimides can be prepared. using any of the procedures available in the art. This invention particularly relates to a new class of sulfimides rearrangement catalysts. These catalysts are selected from the group consisting of:
<Chemistry id="chema03" num="0003"><Image id="ia03" he="13" wi="30" file="IMGA0003.TIF" imgContent="chem" imgFormat="TIFF" inline="no" /></Chemistry>and
<Chemistry id="chema04" num="0004"><Image id="ia04" he="4" wi="40" file="IMGA0004.TIF" imgContent="chem" imgFormat="TIFF" inline="no" /></Chemistry>wherein R, can be a hydrogen, a lower alkyl or an - NH - alkyl and R<Sub>2</Sub> can be a hydrogen, a lower alkyl, aryl or a
<Chemistry id="chema05" num="0005"><Image id="ia05" he="11" wi="26" file="IMGA0005.TIF" imgContent="chem" imgFormat="TIFF" inline="no" /></Chemistry>provided that R, and R<Sub>2</Sub> are not both hydrogens, or R, and R<Sub>2</Sub> can be joined to form a cyclic compound having up to a 7- member ring, and R<Sub>3</Sub> and R<Sub>4</Sub> can be a hydrogen, or a lower alkyl; provided that R<Sub>3</Sub> and R<Sub>4</Sub> are not both hydrogens, or R<Sub>3</Sub> and R<Sub>4</Sub> can be joined to form a cyclic compound having up to a 7-member ring, especially from the group consisting of succinimide, imidazole, glutarimide, phthalimide, 2-pyrrolidone, 2-imidazolidone and cyanuric acid.