Malononitrile → 4-[[2-(benzenesulfonyl)phenyl]hydrazinylidene]pyrazole-3,5-diamine

Reaction equation

C1(S(C2C=CC=CC=2N[N:17]=[C:18]([C:21]#[N:22])[C:19]#[N:20])(=O)=O)C=CC=CC=1.[C:23]1([S:29]([C:32]2[CH:38]=[CH:37][CH:36]=[CH:35][C:33]=2[NH2:34])(=[O:31])=[O:30])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C(#N)CC#N.O.[NH2:45][NH2:46]>>[C:23]1([S:29]([C:32]2[CH:38]=[CH:37][CH:36]=[CH:35][C:33]=2[NH:34][N:17]=[C:18]2[C:19]([NH2:20])=[N:46][N:45]=[C:21]2[NH2:22])(=[O:31])=[O:30])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

Reactant 4

HCID 8010Malononitrile

HCID 24654Hydrazine hydrate (1:1)2×

HCID 77956Benzenamine, 2-(phenylsulfonyl)-

HCID 219550612-[(2-Benzenesulfonylphenyl)hydrazono]malononitrile

Product 1

HCID 1785091784-[[2-(benzenesulfonyl)phenyl]hydrazinylidene]pyrazole-3,5-diamine

Procedure

4-[(2-benzenesulfonylphenyl)hydrazono]-4H-pyrazole-3,5-diamine was prepared using 94 mg (0.5 mmol) of 2-[(2-benzenesulfonylphenyl)hydrazono]malononitrile, which was derived from 2-(phenylsulfonyl)aniline (233 mg, 1.0 mmol) and malononitrile (1.5 mmol), and hydrazine hydrate. Precipitate formed in the reaction tube approximately 20 minutes after the addition of hydrazine hydrate. The resulting solid was isolated by filtration, washed with ethanol, and dried to yield 68 mg (20%) of the compound as an orange coloured solid.