Malononitrile → HCID 178509188, compound

HRID 254962Notes

Reaction equation

HRID 254962 reaction equation
FC1C=C(N[N:10]=[C:11]([C:14]#[N:15])[C:12]#[N:13])C=CC=1F.[F:16][C:17]1[CH:18]=[C:19]([CH:21]=[CH:22][C:23]=1[F:24])[NH2:20].C(#N)CC#N.O.[NH2:31][NH2:32]>>[F:16][C:17]1[CH:18]=[C:19]([NH:20][N:10]=[C:11]2[C:12]([NH2:13])=[N:32][N:31]=[C:14]2[NH2:15])[CH:21]=[CH:22][C:23]=1[F:24]

Participants

5

Reactant 4

HCID 8010MalononitrileHCID 24654Hydrazine hydrate (1:1)2×HCID 774693,4-DifluoroanilineHCID 21954996HCID 21954996, compound

Product 1

HCID 178509188HCID 178509188, compound

Procedure

4-[(3,4-difluorophenyl)hydrazono]-4H-pyrazole-3,5-diamine was prepared using 103 mg (0.5 mmol) of 2-[(3,4-difluorophenyl)hydrazono]malononitrile, which was derived from 3,4-difluoroaniline (99 μL, 1.0 mmol) and malononitrile (1.5 mmol), and hydrazine hydrate. Precipitate formed in the reaction tube approximately 5 minutes after the addition of hydrazine hydrate. The resulting solid was isolated by filtration, washed with ethanol, and dried to yield 45 mg (38%) of the compound as a yellow solid; 1H NMR (ppm, DMSO-d6): 6.18 (br s, 4H), 7.28-7.55 (m, 2H), 7.70-7.82 (m, 1H), 10.80 (br s, 1H).

Workup

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

Sources & evidence

ORD record
ord-c8a22719f8ae44a38122a08fb510959a
Source dataset
uspto-grants-2011_01
Patent number
US07875728B2

Reaction notes

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