4-Cyanophenylacetonitrile → 4-[5-Amino-1-(2,4-dichloro-phenyl)-1H-[1,2,3]triazol-4-yl]-benzonitrile

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Reaction Steps

To a stirred and ice-cooled solution of sodium methoxide (0.388 g, 7.1802 mmol) in methanol (30 ml), 4-cyanophenylacetonitrile (0.817 g, 5.7442 mmol) and 1-azido-2,4-dichloro-benzene (0.900 g, 4.7868 mmol) are added portion wise under a nitrogen atmosphere. The reaction mixture is allowed to attain room temperature spontaneously overnight, concentrated in vacuo, added water and extracted with ethylacetate (3×100 ml). The combined organic layers are dried over MgSO4, filtered and evaporated to give a dark brown gummy residue (1.425 g, 90% mass balance). This crude material is purified by column chromatography over silica gel (230-400 mesh) eluting with 20% ethylacetate in petroleum ether, to afford the title compound as a yellow solid (0.450 g, 29% yield). LC-ESI-HRMS of [M+H]+ shows 330.0319 Da. Calc. 330.031326 Da, dev. 1.7 ppm.

Provenance & Evidence