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

HRID 2095141Notes

Reaction equation

HRID 2095141 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

5

Reactant 4

HCID 8010MalononitrileHCID 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.

Workup

  1. customPrecipitate formed in the reaction tube approximately 20 minutes
  2. customThe resulting solid was isolated by filtration
  3. washwashed with ethanol
  4. customdried

Sources & evidence

ORD record
ord-f38b3488475d4909ac278d3eac0ea919
Source dataset
uspto-grants-2013_05
Patent number
US08445694B2

Reaction notes

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