反应详情

A solution of 3 (9.75 g, 0.65 mol) in dichloromethane (75 mL) under argon was treated with a solution of 1,1′-thiocarbonyldiimidazole in dichloromethane (12.16 g, 0.068 mol) added over 45 min. The reaction was stirred for 15 min after the addition was complete and HPLC analysis indicated complete reaction. The reaction mixture was diluted with dichloromethane (200 mL) and washed with water (3×100 mL) and brine (100 mL). The organic solution was filtered through 1PS filter paper and evaporated under reduced pressure to give a yellow solid. The solid was suspended in 100 mL of 10% hexane-ethyl acetate and filtered. The filter cake was washed with 50 mL of 10% hexane-ethyl acetate and air dried to give 11.2 g (90% yield) of 4. HPLC analysis indicated 99% purity. NMR (CDCl3:d6-DMSO) δ 7.8 (S br, 2H), 7.4 (S, 5H), 4.0–4.7 (m, 1H), 3.3–3.9 (m, 2H), 2.7–3.2 (m, 2H).

1. additionadded over 45 min
2. additionafter the addition
3. customreaction
4. washwashed with water (3×100 mL) and brine (100 mL)
5. filtrationThe organic solution was filtered through 1PS filter paper
6. customevaporated under reduced pressure
7. customto give a yellow solid
8. filtrationfiltered
9. washThe filter cake was washed with 50 mL of 10% hexane-ethyl acetate and air
10. customdried