(5-Chloro-2-methoxyphenyl)acetonitrile → 5-(5-Chloro-2-methoxy-phenyl)-3-(2,4-dichloro-phenyl)-3H-[1,2,3]triazol-4-ylamine

To an ice-cooled and stirred mixture of 1-azido-2,4-dichloro-benzene (0.9 g, 1 eq) and commercial (5-chloro-2-methoxy-phenyl)-acetonitrile (1.04 g, 1.2 eq) in ethanol (10 ml) kept under nitrogen, a solution of sodium methoxide (0.388 g, 1.5 eq) in ethanol (10 ml) is added drop-wise (20 min). After the addition, the reaction mixture is allowed to reach room temperature spontaneously and stirring is then continued overnight at room temperature. The resulting reaction mixture is diluted with ethyl acetate (40 ml), washed with water (2×50 ml), dried over MgSO4 and evaporated to dryness. The yellow solid residue (0.820 g) is purified by crystallization from a mixture of dichloromethane and hexane (1:1), to afford the title compound as white solid (0.480 g, 28% yield). M.p. 153.5-154.7° C.

1. additionAfter the addition
2. customto reach room temperature
3. stirringstirring
4. customThe resulting reaction mixture
5. washwashed with water (2×50 ml)
6. dry with materialdried over MgSO4
7. customevaporated to dryness
8. customThe yellow solid residue (0.820 g) is purified by crystallization from a mixture of dichloromethane and hexane (1:1)

ORD record

ord-923c76d36232492d81b4e1f111027d14

Source dataset

uspto-grants-2012_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08110588B2