N,N'-Bis(dimethylaminomethylene)hydrazine → HCID 20474282, compound

Participants

Reaction Steps

17.3 g (50.0 mmols) of 3-(4-aminophenyl)-7-(4-ethyl-5-methyl-2H-1,2,3-triazol-2-yl)-coumarin, 10.5 g (75.0 mmols) of 1,2-bis-(dimethylaminomethylene)-hydrazine and 200 mg of 4-methylbenzenesulphonic acid are refluxed in 40 ml of anhydrous dimethylformamide for 10 hours under an N2 atmosphere. A further 3.50 g (25.0 mmols) of 1,2-bis-(dimethylaminomethylene)-hydrazine are then added, and the mixture is refluxed for a further 10 hours. 16.1 g (81%) of pale yellow crystals are precipitated on cooling the mixture. Recrystallisation from dimethylformamide yields 14.3 g (72%) of 3-(4-(1,2,4-triazol-4-yl)-phenyl)-7-(4-ethyl-5-methyl-2H-1,2,3-triazol-2-yl)-coumarin in the form of small pale yellow crystals of melting point 321°-323° C.

Provenance & Evidence