Реакция #48187

Уравнение реакции

ethyl acetate

Sodium hydride

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

1,10-dibromodecane

→

title compound

4-[(10-Bromo-decyl)-[1,2,4]triazol-4-yl-amino]-benzonitrile

Растворители

DMSO

Условия реакции

Обработка

1. 1
   workup.ADDITIONwas added
2. 2
   ДругоеThe mixture was transferred into a separation funnel
3. 3
   Экстракцияextracted with water (twice 100 mL) and brine (20 mL)
4. 4
   СушкаThe organic layer was dried over sodium sulphate
5. 5
   Концентрированиеconcentrated under reduced pressure (water bath temperature <30° C.)
6. 6
   workup.ADDITIONThe resulting orange oil was mixed with diethyl ether (100 mL)
7. 7
   Фильтрацияfiltered through a layer of silica (ca. 5 cm)
8. 8
   ПромывкаThe silica was washed with more diethyl ether (ca. 100 mL)
9. 9
   Другоеto remove the excess of 1,10-dibromodecane
10. 10
    ПромывкаThe crude product was washed from the silica with acetone (120 mL)
11. 11
    КонцентрированиеThe acetone solution was concentrated under reduced pressure
12. 12
    Другоеthe residue was purified by column-chromatography (eluent: ethyl acetate)

Методика

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 1,10-dibromodecane (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 1,10-dibromodecane. 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 pale yellow solid. Yield: 1.32 g (65%). 1H-NMR (400 MHz, d6-DMSO) δ=1.16-1.40 (m, 14H), 1.76 (tt, J=7.0, 7.0 Hz, 2H), 3.50 (t, J=6.6 Hz, 2H), 3.79 (t, J=7.0 Hz, 2H), 6.61 (d, J=9.0 Hz 2H), 7.70 (d, J=9.0 Hz, 2H), 8.95 (s, 2H).

Источник