Method of making 5,6-dihydro-2-methyl-N-phenyl-1,4-oxathiin-3-carboxamide

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United States of America Patent

PATENT NO 4247707
SERIAL NO

06071628

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Abstract

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This 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-oxathiolane-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 oxathiolane, 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 a 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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Patent Owner(s)

  • UNIROYAL CHEMICAL CO./UNIROYAL CHEMICAL CIE;UNIROYAL LTD.

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Inventor(s)

Inventor Name Address # of filed Patents Total Citations
Brewer, Arthur D R.R. 1, Puslinch, Ontario, CA 12 64
Znotins, Andrew A 57 Burns Dr., Guelph, Ontario, CA 2 11

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