Malononitrile → HCID 178509173, compound

HRID 254956Notes

Reaction equation

HRID 254956 reaction equation
BrC1C=C(N[N:9]=[C:10]([C:13]#[N:14])[C:11]#[N:12])C=CC=1.[Br: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]>>[Br: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 115623-BromoanilineHCID 24654Hydrazine hydrate (1:1)2×HCID 4199189HCID 4199189, compound

Product 1

HCID 178509173HCID 178509173, compound

Procedure

4-[(3-bromophenyl)hydrazono]-4H-pyrazole-3,5-diamine was prepared using 125 mg (0.5 mmol) of 2-[(3-bromophenyl)hydrazono]malononitrile, which was derived from 3-bromoaniline (172 mg, 1.0 mmol) and malononitrile (1.5 mmol), and hydrazine hydrate. The hydrazine hydrate was added to the solution at a temperature of 75° C. despite the fact that the starting material had not fully dissolved. The solution cleared briefly and then a precipitate formed. The resulting solid was isolated by filtration, washed with ethanol, and dried to yield 93 mg (66%) of the compound as an orange solid; 1H NMR (ppm, DMSO-d6): 6.2 (br s, 4H), 7.21-7.32 (m, 2H), 7.50-7.62 (m, 1H), 7.90 (s, 1H), 10.71 (s, 1H).

Workup

  1. dissolutionhad not fully dissolved
  2. customa precipitate formed
  3. customThe resulting solid was isolated by filtration
  4. washwashed with ethanol
  5. customdried

Sources & evidence

ORD record
ord-fd287be1f29e4efba18795f20e6765e4
Source dataset
uspto-grants-2011_01
Patent number
US07875728B2

Reaction notes

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