Ethyl N-cyanoethanimideate → HCID 178464619, compound

Participants

Reaction Steps

A mixture of trans-4-amino-3,4-dihydro-2,2-dimethyl-3-hydroxy-2H-1-benzopyran-6-carbonitrile (15.28 g) and ethyl N-cyanoacetimidate (9.42 g) in pyridine (70 ml) was refluxed under nitrogen atmosphere for 9 hours. The mixture was cooled to room temperature and concentrated under reduced pressure. The residue was dissolved in ethyl acetate (150 ml), washed with 5% hydrochloric acid (100 ml), water (100 ml), and brine (100 ml), successively. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was recrystallized from ethyl acetate to give trans-4-[N-[1-(cyanoimino)ethyl]amino]-3,4-dihydro-2,2-dimethyl-3-hydroxy-2H-1-benzopyran-6-carbonitrile (12.68 g).

Provenance & Evidence