反应详情

To a solution of 3-(3,5-difluorophenyl)propyl isothiocyanate (0.0177 mol) in dimethylformamide (35 ml) was added water (12 ml), followed by sodium azide (0.0361 mol). The reaction was stirred one hour, then it was diluted with water and washed with ethyl acetate. The aqueous phase was acidified with 3N aqueous hydrogen chloride, extracted into ethyl acetate, washed with water, dried over sodium sulfate and was concentrated. The residue was dissolved in ethyl ether and dicyclohexylamine (1.9 ml) was added. The resulting salt was filtered and partitioned, with stirring, between ethyl ether and 3N aqueous hydrogen chloride. The ethereal layer was washed with water, dried over sodium sulfate and concentrated. The crude product was recrystallized from pet. ether to yield 1.2 g (27%) white crystals: mp 80°-81° (pet. ether).

1. washwashed with ethyl acetate
2. extractionextracted into ethyl acetate
3. washwashed with water
4. dry with materialdried over sodium sulfate
5. concentrationwas concentrated
6. dissolutionThe residue was dissolved in ethyl ether
7. additiondicyclohexylamine (1.9 ml) was added
8. filtrationThe resulting salt was filtered
9. custompartitioned
10. stirringwith stirring, between ethyl ether and 3N aqueous hydrogen chloride
11. washThe ethereal layer was washed with water
12. dry with materialdried over sodium sulfate
13. concentrationconcentrated
14. customThe crude product was recrystallized from pet. ether