تفاعل #11985

معادلة التفاعل

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

المذيبات

DMSO

ظروف التفاعل

المعالجة

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

الإجراء التجريبي

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)

المصدر