Reacción #2310084

Ecuación de reacción

4-mercaptothiophenol

trans-2-Bromomethyl-cyclohexanecarboxylic acid cyanomethylamide

cesium carbonate

→

title compound

trans-N-cyanomethyl-2-[4-(4-sulfanylphenylsulfanyl)-phenylsulfanylmethyl)-cyclohexanecarboxamide

Disolventes

Acetone

acetone

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrovial fitted with a stir bar
2. 2
   Otroa vent cap
3. 3
   Filtraciónfiltered through Celite™
4. 4
   LavadoThe Celite™ was washed with hot acetone (25 mL)
5. 5
   LavadoThe filtrate and wash
6. 6
   Otrothe solvent was removed on a rotary evaporator

Procedimiento

trans-2-Bromomethyl-cyclohexanecarboxylic acid cyanomethylamide (259 mg) and cesium carbonate (340 mg) were weighed into a 15 mL vial fitted with a stir bar and a vent cap. Acetone (3 mL) and 4-mercaptothiophenol (256 mg) were added. The reaction mixture was stirred at 50° C. overnight and then diluted with hot acetone (7 mL) and filtered through Celite™. The Celite™ was washed with hot acetone (25 mL). The filtrate and wash were combined and the solvent was removed on a rotary evaporator. Chromatography of the crude product on C-18 reverse-phase HPLC provided the title compound as a cream solid. 1H NMR (DMSO-d6): δ=8.65 (1H, t), 7.46 (2H, dd), 7.27 (4H, d), 7.21 (2H, dd), 4.12 (2H, d), 3.50 (1H, br m), 2.98 (1H, d), 2.6 (1H, m), 2.1 (2H, m), 1.7 (4H, m), 1.1 (4H, m).

Fuente