反应 #48179

反应方程式

4-[(2-bromo-ethyl)-[1,2,4]triazol-4-yl-amino]-benzonitrile

3-(tert-butyl-dimethylsiloxy)-thiophenol

potassium carbonate

ethyl acetate

→

4-{[2-(3-Hydroxy-phenylsulfanyl)-ethyl]-[1,2,4]triazol-4-yl-amino}-benzonitrile

溶剂

DMF

water

反应条件

后处理

1. 1
   其他The mixture was transferred into a separation funnel
2. 2
   其他The organic layer was separated
3. 3
   洗涤washed with brine (30 mL)
4. 4
   干燥dried over sodium sulphate
5. 5
   浓缩concentrated under reduced pressure
6. 6
   其他The residue was crystallised from methanol

实验过程

A mixture of 4-[(2-bromo-ethyl)-[1,2,4]triazol-4-yl-amino]-benzonitrile (CAB02148=CAB03031, 146 mg, 0.50 mmol), 3-(tert-butyl-dimethylsiloxy)-thiophenol (240 mg, 1.0 mmol) and potassium carbonate (276 mg, 2.0 mmol) in DMF (10 mL) was stirred for 48 hours at room temperature. The mixture was transferred into a separation funnel and ethyl acetate (50 mL) and water (50 mL) were added. The organic layer was separated, washed with brine (30 mL), dried over sodium sulphate and concentrated under reduced pressure. The residue was crystallised from methanol. Yield: 93 mg (55%) to colourless crystals. 1H-NMR (400 MHz, d6-DMSO) δ=3.14 (t, J=7.0 Hz, 2H), 4.02 (t, J=7.0 Hz, 2M, 6.53 (d, J=9.0 Hz, 2H), 6.62 (ddd, J=7.8, 2.0, 0.8 Hz, 1H), 6.70-6.72 (m, 2H), 7.10 (dd, J=7.8, 7.8, 1H), 7.70 (d, J=9.0 Hz, 2H), 8-94 (s, 2H), 9.60 (s, 1H, —OH). 13C-NMR (100 MHz, d6-DMSO) δ=29.53, 52.46, 102.38, 112.86, 113.57, 115.36, 119.00, 130.11, 133.94, 135.82, 143.50, 150.71, 157.90, 169.59. LRMS (FAB+): 338.2 (100, [M+H]+). Found: C, 60.6; H, 4.53; N, 20.8%; C17H15N5OS (337.4) requires C, 60.52; H, 4.48; N, 20.76%.

来源