Malononitrile → HCID 178509182, compound

HRID 254950Notes

Reaction equation

HRID 254950 reaction equation
FC1C=C(N[N:9]=[C:10]([C:13]#[N:14])[C:11]#[N:12])C=CC=1.[F:15][C:16]1[CH:17]=[C:18]([CH:20]=[CH:21][CH:22]=1)[NH2:19].C(#N)CC#N.O.[NH2:29][NH2:30]>>[F:15][C:16]1[CH:17]=[C:18]([NH:19][N:9]=[C:10]2[C:11]([NH2:12])=[N:30][N:29]=[C:13]2[NH2:14])[CH:20]=[CH:21][CH:22]=1

Participants

5

Reactant 4

HCID 8010MalononitrileHCID 97423-FluoroanilineHCID 24654Hydrazine hydrate (1:1)2×HCID 4199695HCID 4199695, compound

Product 1

HCID 178509182HCID 178509182, compound

Procedure

4-[(3-fluorophenyl)hydrazono]-4H-pyrazole-3,5-diamine was prepared using 94 mg (0.5 mmol) of 2-[(3-fluorophenyl)hydrazono]malononitrile, which was derived from 3-fluoroaniline (96 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 41 mg (37%) of the compound as a yellow solid. 1H NMR (ppm, DMSO-d6): 6.2 (br s, 4H), 7.0 (t, 1H), 7.35-7.62 (m, 3H), 10.80 (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-1a10891ef31f49d3931cf1d5d4f3812a
Source dataset
uspto-grants-2011_01
Patent number
US07875728B2

Reaction notes

Loading…