Reaction #48181

Reaction equation

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

4-hydroxy-thiophenol

potassium carbonate

ethyl acetate

→

4-{[3-(4-Hydroxy-phenylsulfanyl)-propyl]-[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 purified by column chromatography (eluent: ethyl acetate, Rf: 0.31)
7. 7
   Otherto give an yellow oil, which
8. 8
   Otherwas crystallised from methanol

Procedure

A mixture of 4-[(2-bromo-propyl)-[1,2,4]triazol-4-yl-amino]-benzonitrile (CAB02180, 146 mg, 0.50 mmol), 4-hydroxy-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 purified by column chromatography (eluent: ethyl acetate, Rf: 0.31) to give an yellow oil, which was crystallised from methanol. Yield: 211 mg (60%). 1H-NMR (400 MHz, d6-DMSO) δ=1.64 (tt, J=7.0, 7.0 Hz, 2H), 2.89 (t, J=7.0 Hz, 2H), 3.92 (t, J=7.0 Hz, 2H), 6.57 (d, J=9.0 Hz, 2H), 6.72 (d, J=9.0 Hz, 2H), 7.20 (d, J=9.0 Hz, 2H), 7.71 (d, J=9.0 Hz, 2H), 8.96 (s, 2H), 9.59 (s, 1H, —OH). LRMS (FAB+): 352.1 (100, [M+H]+).

Source