Reacción #75567

Ecuación de reacción

2-[2-(5-Bromo-2-methoxy-phenyl)-ethyl]-3-chloro-dithiobenzoic acid ethyl ester

trans-1,2 diaminocyclohexane

HCl

→

product

2-{2[2-(5-Bromo-2-methoxy-phenyl)-ethyl]-3-chloro-phenyl}-3a,4,5,6,7,7a-hexahydro-1H-benzoimidazole

Disolventes

water

Condiciones de reacción

Tratamiento posterior

1. 1
   Extracciónextracted with methylene chloride twice
2. 2
   LavadoThe organic extracts were washed with brine
3. 3
   Secadodried (MgSO4)
4. 4
   Otroevaporated
5. 5
   OtroThe residue was chromatographed on silica gel (eluting with 95:5 CH2Cl2/methanol)
6. 6
   Otroto give a yellow oil
7. 7
   Otroevaporated

Procedimiento

As shown in Scheme 12, a solution of 187 mg (0.43 mmol) of 2-[2-(5-Bromo-2-methoxy-phenyl)-ethyl]-3-chloro-dithiobenzoic acid ethyl ester in 2.5 mL of trans-1,2 diaminocyclohexane was heated to 110° C. in a sealed pressure tube for 12 hours. The reaction mixture was diluted with water and extracted with methylene chloride twice. The organic extracts were washed with brine, dried (MgSO4) and evaporated. The residue was chromatographed on silica gel (eluting with 95:5 CH2Cl2/methanol) to give a yellow oil. The oil was treated with methanolic HCl and evaporated to yield 34 mg of product as a pure hydrochloride salt.

Fuente