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

HRID 2295901Notes

Reaction equation

HRID 2295901 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9](=[O:26])[O:10][C:11]3[C:16]([CH:17]=2)=[CH:15][CH:14]=[C:13]([N:18]2[N:22]=[C:21]([CH2:23][CH3:24])[C:20]([CH3:25])=[N:19]2)[CH:12]=3)=[CH:4][CH:3]=1.CN([CH:30]=[N:31][N:32]=[CH:33]N(C)C)C>CN(C)C=O.CC1C=CC(S(O)(=O)=O)=CC=1>[N:31]1[N:32]=[CH:33][N:1]([C:2]2[CH:7]=[CH:6][C:5]([C:8]3[C:9](=[O:26])[O:10][C:11]4[C:16]([CH:17]=3)=[CH:15][CH:14]=[C:13]([N:18]3[N:22]=[C:21]([CH2:23][CH3:24])[C:20]([CH3:25])=[N:19]3)[CH:12]=4)=[CH:4][CH:3]=2)[CH:30]=1

Participants

5

Reactant 2

HCID 3725062N,N'-Bis(dimethylaminomethylene)hydrazine2×HCID 20474268HCID 20474268, compound

Product 1

HCID 20474282HCID 20474282, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 6228DimethylformamideSolvent

Procedure

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.

Workup

  1. temperaturethe mixture is refluxed for a further 10 hours
  2. custom16.1 g (81%) of pale yellow crystals are precipitated
  3. temperatureon cooling the mixture
  4. customRecrystallisation from dimethylformamide

Sources & evidence

ORD record
ord-416bcc66a1a34298a6b6b37af8673fd0
Source dataset
uspto-grants-1984_01
Patent number
US04426530

Reaction notes

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