反应详情

N-Cyano-N'-methyl-O-phenylisourea (0.471 g, 2.69 mmol) was added during 2 minutes to aziridine (0.521 g, 12.1 mmol) at 20° with stirring. Immediate solution occurred, some heat was evolved, and after 5 min a solid precipitate was formed. After 90 min excess aziridine was removed in an air stream at 20°, leaving an oily solid residue. This was dissolved in acetonitrile (10 ml) and the solution was absorbed on to silica gel (1.0 g), and remaining volatiles were removed by evaporation under reduced pressure at 20°. The solid obtained was added to the top of a column of silica gel (19.7 g, length 15 cm, diameter 2 cm) and the column eluted with acetonitrile. The elution of phenol was followed by TLC and after it was complete, subsequent eluate was collected and gave on evaporation to dryness under reduced pressure N-cyano-N'-methyl-1-aziridinoamidine (0.257 g, 77%), m.p. 130°-132.5°, Rf 0.64-0.66 (silica, acetonitrile).

1. customafter 5 min a solid precipitate was formed
2. customAfter 90 min excess aziridine was removed in an air stream at 20°
3. customleaving an oily solid residue
4. customthe solution was absorbed on to silica gel (1.0 g)
5. customwere removed by evaporation under reduced pressure at 20°
6. customThe solid obtained
7. additionwas added to the top of a column of silica gel (19.7 g, length 15 cm, diameter 2 cm)
8. washthe column eluted with acetonitrile
9. washThe elution of phenol
10. customsubsequent eluate was collected