2-hydroxy-N-methyl-N-phenylacetamide

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

Procedure: 0.99 g (6.0 mmole) of N-methyl-N-phenyl-2-hydroxyacetamide was dissolved in THF (6 ml) and the solution was mixed with 0.75 g (6.0 mmole) of 90% potassium t-butoxide with ice cooling. The mixture was stirred for 30 minutes and then 1.24 g (5.0 mmole) of 3-trifluoromethyl-4-phenyl-5-chloroisoxazole was added dropwise to the mixture. After being stirred for 30 minutes, the mixture was refluxed for 24 hours. After cooling the reaction mixture, 60 ml of methylene chloride was added and the mixture was washed with a 5% solution of HCl and water. The methylene chloride phase was evaporated under reduced pressure and the residue was purified by chromatography on silica gel to give 1.15 g of colorless crystals. These were recrystallized from n-hexane to give 950 mg of the titled compound, yield 50.5%, m.p. 93.0°-94.0° C. After being stirred for 30 minutes the mixture was refluxed for 24 hours was added the mixture was washed with a 5% solution of HCl and water The methylene chloride phase was evaporated under reduced pressure the residue was purified by chromatography on silica gel

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

Procedure: 0.99 g (6.0 mmole) of N-methyl-N-phenyl-2-hydroxyacetamide was dissolved in THF (6 ml) and the solution was mixed with 0.75 g (6.0 mmole) of 90% potassium t-butoxide with ice cooling. The mixture was stirred for 30 minutes and then 1.24 g (5.0 mmole) of 3-trifluoromethyl-4-phenyl-5-chloroisoxazole was added dropwise to the mixture. After being stirred for 30 minutes, the mixture was refluxed for 24 hours. After cooling the reaction mixture, 60 ml of methylene chloride was added and the mixture was washed with a 5% solution of HCl and water. The methylene chloride phase was evaporated under reduced pressure and the residue was purified by chromatography on silica gel to give 1.15 g of colorless crystals. These were recrystallized from n-hexane to give 950 mg of the titled compound, yield 50.5%, m.p. 93.0°-94.0° C. After being stirred for 30 minutes the mixture was refluxed for 24 hours was added the mixture was washed with a 5% solution of HCl and water The methylene chloride phase was evaporated under reduced pressure the residue was purified by chromatography on silica gel

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

Procedure: 5.8 g (0.025 mol) of 2-methylsulphonyl-5-trifluoromethyl-1,3,4-thiadiazole, 4.4 g (0.026 mol) of N-methyl-2-hydroxyacetanilide, 3.8 g (0.038 mol) of potassium carbonate, 0.5 g of tetraethylammonium bromide and 50 ml of acetone are mixed in a 100 ml three-necked flask equipped with a stirrer and a thermometer, and the mixture is stirred for 20 hours at 20°-25° C. The undissolved salts are then filtered off and washed with acetone and the whole of the filtrate is freed of solvent in vacuo. The residue is taken up in 100 ml of diethyl ether, washed with dilute hydrochloric acid, dried over sodium sulphate and filtered, and the filtrate is freed of solvent in vacuo. The remaining oil crystallizes completely after a short time. 7.2 g (90.8% of theory) of 2-(5-trifluoromethyl-1,3,4-thiadiazol-2-yloxy)-N-methylacetanilide of melting point 63° C. are obtained. equipped with a stirrer The undissolved salts are then filtered off washed with acetone washed with dilute hydrochloric acid dried over sodium sulphate filtered The remaining oil crystallizes completely after a short time

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

Procedure: 0.99 g (6.0 mmole) of N-methyl-N-phenyl-2-hydroxyacetamide was dissolved in THF (6 ml) and the solution was mixed with 0.75 g (6.0 mmole) of 90% potassium t-butoxide with ice cooling. The mixture was stirred for 30 minutes and then 1.24 g (5.0 mmole) of 3-trifluoromethyl-4-phenyl-5-chloroisoxazole was added dropwise to the mixture. After being stirred for 30 minutes, the mixture was refluxed for 24 hours. After cooling the reaction mixture, 60 ml of methylene chloride was added and the mixture was washed with a 5% solution of HCl and water. The methylene chloride phase was evaporated under reduced pressure and the residue was purified by chromatography on silica gel to give 1.15 g of colorless crystals. These were recrystallized from n-hexane to give 950 mg of the titled compound, yield 50.5%, m.p. 93.0°-94.0° C. After being stirred for 30 minutes the mixture was refluxed for 24 hours was added the mixture was washed with a 5% solution of HCl and water The methylene chloride phase was evaporated under reduced pressure the residue was purified by chromatography on silica gel