Method of making 5,6-dihydro-2-methyl-n-phenyl-l,4-...

Details Method of making 5,6-dihydro-2-methyl-n-phenyl-l,4-... Method of making 5,6-dihydro-2-methyl-n-phenyl-l,4-...

C - Chemistry, Metallurgy

07

D

260/327.7

C07D 327/04 (2006.01) C07D 327/06 (2006.01)

Patent

CA 1118429

ABSTRACT OF THE DISCLOSURE 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-mercap- toethanol wlth 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 loxathiolane 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 quaternary ammonium salt to form 5,6-dihydro-2-methyl-N-phenyl-1,4-oxathiin-3-carboxa- mide with evolutlon of water. The product is a known bactericide and fungicide.

371748

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