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

HRID 2304442Notes

Reaction equation

HRID 2304442 reaction equation
[C:1]1([S:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[NH:16][N:17]=[C:18]([C:21]#[N:22])[C:19]#[N:20])(=O)=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1(S(C2C=CC=CC=2N)(=O)=O)C=CC=CC=1.C(#N)CC#N.[OH2:44].[NH2:45][NH2:46]>>[NH2:22][C:21]1[C:18](=[N:17][NH:16][C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[S:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)(=[O:8])=[O:44])[C:19]([NH2:20])=[N:46][N:45]=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-diamineYield 20%

Procedure

This compound 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) as described in Example 8, and hydrazine hydrate. Precipitate formed in the reaction tube approximately 20 min 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 title compound as an orange coloured solid.

Workup

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

Sources & evidence

ORD record
ord-b3a1d2e58ec54a3cac6b974a69d0c395
Source dataset
uspto-grants-2002_08
Patent number
US06436915B1

Reaction notes

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