反应详情

To the solution prepared from 80 ml of methanol and 0.89 g of sodium, 6.53 g of 5-mercaptopyridine-2-carboxylic acid methyl ester are added, followed by the solution of 12.6 g of methyl α-bromo-m-trifluoromethylphenylacetate in 50 ml of methanol while stirring under nitrogen. The mixture is warmed for 1/2 hour on the steam bath and allowed to stand at room temperature overnight. It is evaporated, the residue taken up in water-diethyl ether, the organic phase washed with water, dried and evaporated. The residue is dissolved in the minimum amount of methanolisopropanol (1:1), the solution mixed with 85 ml of N aqueous sodium hydroxide, warmed for 1/2 hour on the steam bath, and stored at room temperature overnight. The mixture is evaporated, the residue taken up in 2 N hydrochloric acid and the mixture extracted with diethyl ether-ethyl acetate (1:1). The extract is washed with water, dried and evaporated and the residue recrystallized from diethyl ether-ethyl acetate, to yield the 5-(α-carboxy-m-trifluoromethylbenzylmercapto)-pyridine-2-carboxylic acid melting at 190°-195°.

1. additionare added
2. temperatureThe mixture is warmed for 1/2 hour on the steam bath
3. customIt is evaporated
4. washthe organic phase washed with water
5. customdried
6. customevaporated
7. dissolutionThe residue is dissolved in the minimum amount of methanolisopropanol (1:1)
8. additionthe solution mixed with 85 ml of N aqueous sodium hydroxide
9. temperaturewarmed for 1/2 hour on the steam bath
10. waitstored at room temperature overnight
11. customThe mixture is evaporated
12. extractionthe mixture extracted with diethyl ether-ethyl acetate (1:1)
13. washThe extract is washed with water
14. customdried
15. customevaporated
16. customthe residue recrystallized from diethyl ether-ethyl acetate