MANUFACTURE OF 22METHYLLNNPHENYLL1*33 OXATHIOLANEE22ACETAMIDEE33OXIDE

Japanese Patent JPS5699469

A

A method of making 5,6-dihydro-2-methyl-N-phenyl-1,4-oxathiin-3-carboxamide is based on the use of an oxathiolane, namely, 2-methyl-N-phenyl-1,3-oxathilane-2-acetamide, which may be formed by condensing 2-mercaptoethanol with acetoacetanilide under acidic conditions in a solvent medium (aromatic hydrocarbon, chlorinated hydrocarbon or alkyl ester of an aliphatic acid). The said oxathilane, with or without purification, is reacted with hydrogen peroxide in water or in a water-organic solvent mixture under basic conditions in the presence of a catalytic amount of a metal compound such as sodium tungstate to form 2-methyl-N-phenyl-1,3-oxathiolane-2-acetamide 3-oxide. The said oxathiolane oxide, while dissolved in a chlorinated hydrocarbon or an alkyl ester of an aliphatic carboxylic acid, or while suspended in an aromatic hydrocarbon, is subjected to a ring expansion reaction by heating under acidic conditions in the presence of a catalytic quantity of an anium compound, i.e., a quaternary ammonium salt or sulfonium, sulfoxonium or phosphonium compound, to form 5,6-dihydro-2-methyl-N-phenyl-1,4-oxathiin-3-carboxamide with evolution of water. The product is a known bactericide and fungicide.

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ANDORIYUU EI ZUNOTEINZU
AASAA DEII BURIYUUAA

JP16733680A

August 10, 1981

November 27, 1980

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UNIROYAL LTD

C07D327/04; C07D327/06; C07D327/08; (IPC1-7): C07D327/06

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