反应详情

To a solution of p-tetradecylbenzenesulfonyl chloride (440 mg, 1.18 mmol) in pyridine (8 mL) was added 1,3,4-thiadiazol-2-amine (179 mg, 1.77 mmol). The reaction mixture was stirred at room temperature for 6 hours, then 2 M HCl (40 mL) was added to quench the reaction. The mixture was extracted with ethyl acetate (3×50 mL), the organic layer was washed with water (40 mL) and brine (40 mL), dried over anhydrous Na2SO4 and concentrated. The residue was purified by chromatography over silica gel (70-230 mesh) eluted with methanol:DCM 1:19 to give the product as a solid (240 mg, 0.55 mmol, 47% yield), mp 116-117° C.; 1H NMR (300 MHz, CDCl3) δ 0.88 (t, 3H, J=6.9 Hz), 1.25 (m, 22H), 1.60 (m, 2H), 2.64 (t, 2H, J=7.2 Hz), 7.29 (d, 2H, J=8.4 Hz), 7.84 (d, 2H, J=8.4 Hz), 8.23 (s, 1H); 13C NMR (75 MHz, CDCl3) 14.1, 22.6, 29.2, 29.3, 29.4, 29.5, 29.6, 31.1, 31.9, 35.9, 126.5, 128.9, 138.1, 142.6, 148.6, 167.4; MS (LCQ, ESI+) Calcd for C22H36N3O2S2 438.2, found 438.3 (M+H)+; HRMS (ESI+, m/z) Calcd for C22H36N3O2S2 438.2243, found 438.2243 (M+H)+.

1. customto quench
2. customthe reaction
3. extractionThe mixture was extracted with ethyl acetate (3×50 mL)
4. washthe organic layer was washed with water (40 mL) and brine (40 mL)
5. dry with materialdried over anhydrous Na2SO4
6. concentrationconcentrated
7. customThe residue was purified by chromatography over silica gel (70-230 mesh)
8. washeluted with methanol:DCM 1:19