反应详情

A solution of potassium thiolacetate is prepared by adding 495 ml. of 2N-methanolic potassium hydroxide (0.99 mole) during a period of 15 min. to a solution of 74.3 ml. of thiolacetic acid (79.1 g., 1.04 mole) and 500 ml. of methanol while maintaining a temperature of 1°-5° C. The methanolic potassium thiolacetate solution thus prepared is added over 0.5 hr. to a mixture of N-[3-(chloroacetylamino)benzoyl]glycine methyl ester (267.5 g., 0.94 mole) in 2 l. of methanol while maintaining a temperature of 0°-5° C. After stirring for a period of 1 hr. without cooling, the reaction mixture is warmed at 40°-45° C. for 2 hrs., cooled, and filtered. The material collected is sequentially washed with 50% methanol, water, and 50% methanol, and then air dried to afford 262.4 g. (86% yield) of N-[3-(acetylthioacetylamino)benzoyl]glycine methyl ester, m.p. 86°-88° C. Crystallization from methanol provides analytically pure N-[3-(acetylthioacetylamino)benzoyl]glycine methyl ester, m.p. 90.0°-92.0° C.

1. additionby adding 495 ml
2. additionis added over 0.5 hr
3. temperaturewithout cooling
4. temperaturethe reaction mixture is warmed at 40°-45° C. for 2 hrs
5. temperature, cooled
6. filtrationfiltered
7. customThe material collected
8. washis sequentially washed with 50% methanol, water, and 50% methanol
9. customair dried
10. customto afford 262.4 g