Reaction #48178

Reaction equation

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

4-hydroxythiophenol

potassium carbonate

ethyl acetate

→

4-{[2-(4-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 (CAB03031, 146 mg, 0.50 mmol), 4-hydroxythiophenol (126 mg, 1.0 mmol) and potassium carbonate (138 mg, 1.0 mmol) in DMF (10 mL) was stirred overnight 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: 116 mg (69%) colourless crystals. 1H-NMR (400 MHz, d6-DMSO) δ=2.99 (t, J=7.0 Hz, 2H), 3.93 (t, J=7.0 Hz, 2H), 6.48 (d, =9.0 Hz, 2H), 6.73 (d, J=8.6 Hz, 2H), 7.21 (d, J=8.6 Hz, 2H), 7.68 (d, J=9.0 Hz, 2H), 8.89 (s, 2H), 9.66 (s, 1H, —OH). 13C (100 MHz, d6-DMSO) δ 30.62, 53.07, 102.92, 113.36, 116.86, 119.59, 122.71, 134.07, 134.49, 144.07, 151.17, 157.83. LRMS (FAB+): 338.2 (100, [M+H]+). Found: C, 60.6; H, 4.57; N, 20.6%; C17H15N5OS (337.4) requires C, 60.52; H, 4.48; N, 20.76%.

Source