Triethylamine → 2,3-Dihydro-3-thioxo-2-(2,6-dioxo-3-piperidinyl)-1H-isoindol-1-one

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Reaction Steps

A mixture of compound 208 (81 mg, 0.276 mmol), trifluoroacetamide (57 mg, 0.50 mmol), 1-hydroxybenzotriazole (145 mg, 1.07 mmol), 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (200 mg, 1.04 mmol) and triethylamine (0.21 mL, 1.51 mmol) in CH2Cl2 (1.5 mL) was stirred at ambient temperature for 3 days. Water (10 mL) and CH2Cl2 (10 mL) were added. The dichloromethane layer was separated, washed with water, dried over Na2SO4 and evaporated under reduced pressure. Purification by chromatography, with EtOAc:CH2Cl2 (1:10) as the eluent, gave compound 212 (48 mg, 63%) as a red solid: mp 255° C.; 1H NMR (CDCl3) δ 8.00-7.98 (m, 1H), 7.80-7.71 (m, 3H), 5.63 (br, 1H), 2.98-2.70 (m, 3H), 2.18-2.15 (m, 1H); MS (CI/CH4) m/z 274 (M+); Anal. (C13H10N2O3S) C, H, N.

Provenance & Evidence