2-(2-methyl-1,3-oxathiolan-2-yl)-N-phenylacetamide

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Cis-2-methyl-N-phenyl-1,3-oxathiolane-2-acetamide-3-oxide, prepared from 0.1 moles of 2-methyl-N-phenyl-1,3-oxathiolane-2-acetamide as prepared in Example 1, was placed with toluene (100 g), tetrabutylammonium bromide (a phase transfer catalyst) (0.32 g, 0.001 g mole) and malonic acid (pKa =2.83, 0.41 g, 0.004 g mole) in a 1 L three-necked round bottom flask equipped with a mechanical stirrer, a thermometer and a Dean-Stark trap for the efficient removal of evolved water of reaction. The reaction mixture so prepared was placed under a vacuum equivalent of 300 mm of Hg and heated at 72°-75° C. for 1 hour. Methanesulfonic acid (0.19 g, 0.002 g mole) was then added to the reaction mixture, the vacuum was increased to 200 mm Hg and heating was continued at 72°-75° C. for an additional hour. The reaction mixture was then cooled to 55°-60° C. and washed successively with 100 mL portions of 5% aqueous sodium hydroxide solution and water. The resulting organic layer was then decanted and concentrated, and after isolation and drying, yielded a total of 17.3 g of 5,6-dihydro-2-methyl-1,4-oxathiin-3-carboxanilide. as prepared in Example 1 equipped with a mechanical stirrer a thermometer and a Dean-Stark trap for the efficient removal of evolved water of reaction The reaction mixture so prepared heated at 72°-75° C. for 1 hour the vacuum was increased to 200 mm Hg heating was continued at 72°-75° C. for an additional hour The reaction mixture was then cooled to 55°-60° C. washed successively with 100 mL portions of 5% aqueous sodium hydroxide solution and water The resulting organic layer was then decanted concentrated after isolation and drying

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: bringing together the 2-methyl-N-phenyl-1,3-oxathiolane-2-acetamide and hydrogen peroxide under basic conditions, in the presence of a catalytic quantity of a suitable heavy metal compound oxidation catalyst effective to catalyze the oxidation of said 2-methyl-N-phenyl-1,3-oxathiolane-2-acetamide by the said hydrogen peroxide, in a liquid medium comprising water, or water plus at least one nonprotic organic liquid selected from the group consisting of (a) aromatic hydrocarbon solvent having a boiling point not greater than 145° C., (b) chlorinated hydrocarbon solvent having a boiling point not greater than 130° C., and (c) a solvent having a boiling point not greater than 130° C. which is an alkyl ester of an aliphatic carboxylic acid, and subjecting the resulting mixture while agitating to a temperature of from 0°-25° C., whereby 2-methyl-N-phenyl-1,3-oxathiolane-2-acetamide 3-oxide is formed;

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: bringing together the 2-methyl-N-phenyl-1,3-oxathiolane-2-acetamide and hydrogen peroxide under basic conditions, in the presence of a catalytic quantity of a suitable heavy metal compound oxidation catalyst effective of catalyze the oxidation of said 2-methyl-N-phenyl-1,3-oxathiolane-2-acetamide by the said hydrogen peroxide, in a liquid medium comprising water, or water plus at least one nonprotic organic liquid selected from the group consisting of (a) aromatic hydrocarbon solvent having a boiling point not greater than 145° C., (b) chlorinated hydrocarbon solvent having a boiling point not greater than 130° C., and, (c) a solvent having a boiling point not greater than 130° C. which is an alkyl ester of an aliphatic carboxylic acid, and subjecting the resulting mixture while agitating to a temperature of from 0° to 25° C., whereby 2-methyl-N-phenyl-1,3-oxathiolane-2-acetamide 3-oxide is formed;