反应详情

To a yellow solution of 4-benzyl-2-nitrophenol (2.0 g, 8.7 mmol) in 20 mL DMF at 0° C. was added sodium hydride (0.38 g, 9.6 mmol). The reaction became deep orange, and after 30 min dimethylthiocarbamoyl chloride (1.2 g, 9.6 mmol) was added. The reaction was stirred over the weekend at room temperature. Water was added, and the mixture was extracted with DCM 3 times. The combined extracts were washed with 0.5M NaHCO3, dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo to give a brown oil. The oil was heated to 160° C. for a total of 2 h. The reaction was cooled, and the resulting oil was loaded directly onto a 120 g ISCO column and eluted with 0-30-50% EtOAc/hexanes, to give S-4-benzyl-2-nitrophenyl dimethylcarbamothioate. MS (ESI) m/z: Calculated: 316.1; Observed: 317.1 (M++1).

1. extractionthe mixture was extracted with DCM 3 times
2. washThe combined extracts were washed with 0.5M NaHCO3
3. dry with materialdried over anhydrous sodium sulfate
4. filtrationfiltered
5. concentrationconcentrated in vacuo
6. customto give a brown oil
7. temperatureThe oil was heated to 160° C. for a total of 2 h
8. temperatureThe reaction was cooled
9. washeluted with 0-30-50% EtOAc/hexanes