1-Azido-4-methoxybenzene → 5-(3,4-Dichlorophenyl)-3-(4-methoxyphenyl)triazol-4-amine

Participants

Reaction Steps

To a stirred and ice-cooled solution of 1-azido-4-methoxy-benzene (2.000 g, 13.4090 mmol) and 3,4-dichlorophenylacetonitrile (2.994 g, 16.0909 mmol) in absolute ethanol (30 ml), an ice-cooled solution of sodium methoxide (1.087 g, 20.1136 mmol) in absolute ethanol (20 ml) is added drop-wise. The resulting reaction mixture is evaporated and the residue is dissolved in methylene chloride and washed with water, brine, dried over MgSO4, filtered and evaporated to afford ˜4.5 g of crude material as brownish solid. This material is purified by crystallization from methylene chloride and petroleum ether, to obtain the title compound as reddish solid (1.536 g, 34% yield). M.p. 189.9-191.3° C. LC-ESI-HRMS of [M+H]+ shows 335.0483 Da. Calc. 335.046642 Da, dev. 4.9 ppm.

Provenance & Evidence