Reacción #48180

Ecuación de reacción

ethyl acetate

Sodium hydride

4-([1,2,4]triazol-4-ylamino)-benzonitrile

1,3-dibromopropane

→

title compound

4-[(3-Bromo-propyl)-[1,2,4]triazol-4-yl-amino]-benzonitrile

Disolventes

DMSO

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONwas added
2. 2
   OtroThe mixture was transferred into a separation funnel
3. 3
   Extracciónextracted with water (twice 100 mL) and brine (20 mL)
4. 4
   SecadoThe organic layer was dried over sodium sulphate
5. 5
   Concentraciónconcentrated under reduced pressure (water bath temperature <30° C.)
6. 6
   workup.ADDITIONThe resulting orange oil was mixed with diethyl ether (100 mL)
7. 7
   Filtraciónfiltered through a layer of silica (ca. 5 cm)
8. 8
   LavadoThe silica was washed with more diethyl ether (ca. 100 mL)
9. 9
   Otroto remove the excess of 1,3-dibromopropane
10. 10
    Lavadothe crude product was washed from the silica with acetone (120 mL)
11. 11
    ConcentraciónThe acetone solution was concentrated under reduced pressure
12. 12
    Otrothe residue was purified by column-chromatography (eluent: ethyl acetate)

Procedimiento

Sodium hydride (60%, 240 mg, 6.0 mmol) was added to a solution of 4-([1,2,4]triazol-4-ylamino)-benzonitrile (926 mg, 5.0 mmol) in DMSO (25 mL) at r.t. The mixture was stirred for 1 hour at this temperature and 1,3-dibromopropane (5 mL) was added. The reaction mixture was stirred overnight and ethyl acetate (100 mL) was added. The mixture was transferred into a separation funnel and extracted with water (twice 100 mL) and brine (20 mL). The organic layer was dried over sodium sulphate and concentrated under reduced pressure (water bath temperature <30° C.). The resulting orange oil was mixed with diethyl ether (100 mL) and filtered through a layer of silica (ca. 5 cm). The silica was washed with more diethyl ether (ca. 100 mL) to remove the excess of 1,3-dibromopropane, the crude product was washed from the silica with acetone (120 mL). The acetone solution was concentrated under reduced pressure and the residue was purified by column-chromatography (eluent: ethyl acetate) to give the title compound as a white solid. Yield: 792 mg (52%). 1H-NMR (400 MHz, d6-DMSO) δ=2.01 (tt, J=7.0, 6.6 Hz, 2H), 3.64 (t, J=6.6 Hz, 2H), 3.95 (t, J=7.0 Hz, 2H), 6.62 (d, J=9.0 Hz, 2H), 7.74 (d, J=9.0 Hz, 2H), 9.02 (s, 2H). 13C-NMR (100 MHz, d6-DMSO) δ=30.38, 32.13, 52.72, 103.17, 113.83, 119.74, 134.63, 144.14, 151.65. LRMS (FAB+): 306.0 (100, [M+H]+).

Fuente