Reaction #48179

Reaction equation

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

Solvents

DMF

water

Conditions

Workup

1. 1
   OtherThe mixture was transferred into a separation funnel
2. 2
   OtherThe organic layer was separated
3. 3
   Washwashed with brine (30 mL)
4. 4
   Dryingdried over sodium sulphate
5. 5
   Concentrationconcentrated under reduced pressure
6. 6
   OtherThe residue was crystallised from methanol

Procedure

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%.

Source