2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 135973970, compound

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Reaction Steps

300 mg of 1-(4-hydroxy-3,5-di-tert.-butylbenzylamino)imidazole are heated to about 60°-70° on a water-bath together with 10 drops of glacial acetic acid in 25 ml of benzene. After the dropwise addition of a solution of 250 mg of dicyanodichlorobenzoquinone in 10 ml of benzene, the mixture is warmed for an additional 15 minutes. The reaction mixture is subsequently cooled in an ice-bath and the separated solid is removed by filtration. The filtrate is shaken with 10% sodium carbonate solution. After separation of the organic phase the aqueous phase is extracted once with benzene. The combined organic phases are dried with anhydrous magnesium sulfate, filtered and evaporated under reduced pressure. The crystalline residue is recrystallized from ethyl acetate/n-hexane and there is obtained 1-(4-hydroxy-3,5-di-tert.-butylbenzylideneamino)imidazole of m.p. 173°.

Provenance & Evidence