反应详情

A suspension of 6-nitro-2-(2-pyrrolidin-1-ylethylamino)benzothiazole (Example 11, 50 mg, 0.17 mmol) and SnCl2 (161 mg, 0.85 mmol) in 20 mL of ethanol (denatured) was heated at reflux for 4 hours. After cooling the mixture was partitioned between 50 mL of ethyl acetate and 20 mL of 1.0N aqueous NaOH. The organic layer was dried over sodium sulfate and concentrated to give a yellow residue which was subjected to silica gel column chromatography (5% 2M NH3/MeOH:95% CH2Cl2). Yield: 65%, 1H-NMR (CD3OD): δ 8.70 (d, 1H, J=8.3 Hz); 8.47 (d, 1H, J=2.0 Hz); 8.21 (dd, 1H, J=6.3, 1.9 Hz); 5.05 (t, 2H, J=6.3 Hz); 4.28 (t, 2H, J=6.8 Hz); 4.14 (m, 4H); 3.33 (m, 4H).

1. temperaturewas heated
2. temperatureat reflux for 4 hours
3. temperatureAfter cooling the mixture
4. customwas partitioned between 50 mL of ethyl acetate and 20 mL of 1.0N aqueous NaOH
5. dry with materialThe organic layer was dried over sodium sulfate
6. concentrationconcentrated
7. customto give a yellow residue which