2,4-Dichlorobenzylidenemalononitrile → HCID 67214669, compound

Participants

Reaction Steps

A solution of 157 mg (1.87 mmol) of 3-amino-1,2,4-triazole and 417 mg (1.87 mmol) of (2,4-dichlorobenzylidene)malononitrile (Intermediate 1) in 4.7 mL of anhydrous pyridine was stirred at reflux under air for 22 h and then cooled and concentrated in vacuo. The residue was partitioned between 5% aqueous citric acid solution and a 1:1 mixture of ethyl acetate and tetrahydrofuran. The organic phase was washed once more with the citric acid solution and then (after addition of some more tetrahydrofuran) with saturated aqueous sodium chloride solution. The combined aqueous fractions were re-extracted with a 2:3 mixture of ethyl acetate and tetrahydrofuran. The combined organics were dried over magnesium sulfate, filtered, and concentrated in vacuo. Purification of the residue by flash chromatography on silica gel (gradient elution with 2-3% methanol in dichloromethane) afforded the title compound as an amber-colored glass, which was used without further purification. LC-MS 305 (M+1).

Provenance & Evidence