Réaction #48178

Équation de réaction

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

Solvants

DMF

water

Conditions de réaction

Traitement

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

Mode opératoire

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