Reaktion #48179

Reaktionsgleichung

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

Lösungsmittel

DMF

water

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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%.

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