反应详情

In a 250 mL round bottom flask was added 2-mercaptobenzonitrile (2.0 g, 14.8 mmol) from Step 1(B) followed by anhydrous DMF (30 mL). Ammonium chloride (1.42 g, 26.64 mmol) and sodium azide (1.73 g, 26.64 mmol) were added to the reaction flask followed by an additional 10 mL of DMF. The reaction mixture was heated to 105° C. under a flow of N2 and stirred overnight. The reaction was worked up by first cooling to room temperature. Next the solution was acidified by the addition of 50 mL of 1N HCl. The solution was extracted with ethyl acetate (2×100 mL) and then washed with brine (100 mL). The combined organics were dried over Na2SO4 and then concentrated under reduced pressure to afford a white solid. The solid was collected by filtration of a heptane/ethyl acetate treatment (7:3, 10 mL) which afforded the title compound as a white solid (1.21 g, 46%); Rf of 0.05″ with 95:5 v/v dichloromethane: methanol; 1H-NMR (400 MHz; DMSO-d6) δ 7.91 (d, 1H), 7.78 (d, 1H), 7.64-7.50 (m, 2H), 2.90 (s, 1H), 2.78 (s, 1H); MS (ESI−) m/z 177.1 (Mz−1).

1. extractionThe solution was extracted with ethyl acetate (2×100 mL)
2. washwashed with brine (100 mL)
3. dry with materialThe combined organics were dried over Na2SO4
4. concentrationconcentrated under reduced pressure
5. customto afford a white solid
6. filtrationThe solid was collected by filtration of a heptane/ethyl acetate treatment (7:3, 10 mL) which