反应 #11985

反应方程式

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

溶剂

DMSO

反应条件

后处理

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

实验过程

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). 4-{[10-(4-Hydroxy-phenylsulfanyl)-decyl]-[1,2,4]triazol-4-yl-amino}-benzonitrile (CAB03011, STX625)

来源