反应详情

A mixture of 4-cyanomethylsulfanylbenzoic acid (27.2 g, 0.14 mol), sodium azide (11.8 g, 0.18 mol) and ammonium chloride (9.7 g, 0.18 mol) in DMF (1000 mL) was refluxed overnight under N2. The mixture was concentrated in vacuo. The residue was suspended in cold water and extracted with diethyl ether. The combined organic phases were washed with brine, dried over Na2SO4 and concentrated in vacuo. Water was added and the precipitate was filtered off. The aqueous layer was concentrated in vacuo, water was added and the precipitate filtered off. The combined impure products were purified by column chromatography using DCM:MeOH=9:1 as eluent, affording the title compound (5.2 g, 16%).

1. temperaturewas refluxed overnight under N2
2. concentrationThe mixture was concentrated in vacuo
3. extractionextracted with diethyl ether
4. washThe combined organic phases were washed with brine
5. dry with materialdried over Na2SO4
6. concentrationconcentrated in vacuo
7. additionWater was added
8. filtrationthe precipitate was filtered off
9. concentrationThe aqueous layer was concentrated in vacuo, water
10. additionwas added
11. filtrationthe precipitate filtered off
12. customThe combined impure products were purified by column chromatography