methyl 2-benzamidoacetate

Conditions: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To 5.8 g. of methyl hippurate dissolved in 35 ml THF was added 3.9 g. of triphenylphosphine and 10.0 g. of carbon tetrachloride in 15 ml THF. The mixture was heated to about 50° C. for 6 hours and 3.0 g. of hydrazine hydrate was added. The mixture was refluxed for about 18 hours, cooled and poured into water. The solution was extracted with ethyl acetate, and the organic phase was then extracted with 1 N HCl. The acidic extract was neutralized with 6 N sodium hydroxide and the product was extracted with ethyl acetate. The organic phase was dried over anhydrous magnesium sulfate and concentrated under vacuum. The solid was recrystallized from methanol to yield about 0.200 g. of solid. Yield 4%. M.P.=212°-216° C. was added 3.9 g The mixture was refluxed for about 18 hours cooled The solution was extracted with ethyl acetate the organic phase was then extracted with 1 N HCl The acidic extract the product was extracted with ethyl acetate The organic phase was dried over anhydrous magnesium sulfate concentrated under vacuum The solid was recrystallized from methanol to yield about 0.200 g

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 1.0 g (5.2 mmol) of benzoylglycin methyl ester and 1.4 g (6.4 mmol) of diphosphorous pentasulfide was added quickly into a reaction vessel. After that, anhydrous chloroform (15 ml) was also added and heated to around 80° C. When decrease in hydrogen sulfide generation and white precipitate formation in the reaction solution were observed, an argon balloon was attached and the solution was refluxed for 24 hours. After completion of reaction, the precipitate was dissolved by adding an aqueous solution of strong alkali to the solution, and the organic phase was extracted with dichloromethane, followed by drying with addition of magnesium sulfate and removal of solvent. The product was developed with ethyl acetate:hexane=5:5 solvent on a silica column to give 5-methoxy-2-phenylthiazole (Rf=0.40). The yield was 566 mg in weight and 57% in percentage. the solution was refluxed for 24 hours After completion of reaction the precipitate was dissolved by adding an aqueous solution of strong alkali to the solution the organic phase was extracted with dichloromethane by drying with addition of magnesium sulfate and removal of solvent