反应详情

A solution of 5.85 g. of methyl 3-(2,6-dichlorobenzylidene)thiocarbazimidate hydriodide and 1.62 g. of 3-(aminomethyl)pyridine in 25 ml. of absolute ethanol is heated under reflux for 47 hours. To the resulting solution is added 3.00 ml. of 5N sodium hydroxide and evaporation under reduced pressure gives a light brown crystalline residue. The residue is dissolved in 100 ml. of dichloromethane:methanol (95:5) and chromatographed on a column (2.8 × 35 cm.) of silica gel; 200 ml. cuts are taken. Evaporation under reduced pressure of combined cuts 2-4 gives 4.70 g. of crude product as a light tan foam. The foam is dissolved in 25 ml. of absolute ethanol and 7.5 ml. of 5.25N methanolic hydrogen chloride is added. The resulting solution is evaporated under reduced pressure and the residual gum is crystallized from absolute ethanol-acetone. After chilling, filtration gives 3.83 g. of light tan crystals. Recrystallization from 1:1 methanol:acetonitrile gives the desired product as colorless crystals, m.p. 235°-239° C. (dec.).

1. temperatureunder reflux for 47 hours
2. additionTo the resulting solution is added 3.00 ml
3. customof 5N sodium hydroxide and evaporation under reduced pressure
4. customgives a light brown crystalline residue
5. dissolutionThe residue is dissolved in 100 ml
6. customof dichloromethane:methanol (95:5) and chromatographed on a column (2.8 × 35 cm.) of silica gel
7. customEvaporation under reduced pressure of combined cuts 2-4
8. customgives 4.70 g
9. dissolutionThe foam is dissolved in 25 ml
10. customThe resulting solution is evaporated under reduced pressure
11. customthe residual gum is crystallized from absolute ethanol-acetone
12. temperatureAfter chilling
13. filtrationfiltration
14. customgives 3.83 g
15. customRecrystallization from 1:1 methanol