Malononitrile → HCID 178509190, compound

HRID 254966Notes

Reaction equation

HRID 254966 reaction equation
ClC1C=C(N[N:10]=[C:11]([C:14]#[N:15])[C:12]#[N:13])C=C(Cl)C=1.[Cl:16][C:17]1[CH:18]=[C:19]([CH:21]=[C:22]([Cl:24])[CH:23]=1)[NH2:20].C(#N)CC#N.O.[NH2:31][NH2:32]>>[Cl: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]=[C:22]([Cl:24])[CH:23]=1

Participants

5

Reactant 4

HCID 8010MalononitrileHCID 122813,5-DichloroanilineHCID 24654Hydrazine hydrate (1:1)2×HCID 2736049(3,5-Dichlorophenyl)carbonohydrazonoyl dicyanide

Product 1

HCID 178509190HCID 178509190, compound

Procedure

4-[(3,5-dichlorophenyl)hydrazono]-4H-pyrazole-3,5-diamine was prepared using 120 mg (0.5 mmol) of 2-[(3,5-dichlorophenyl)hydrazono]malononitrile, which was derived from 3,5-dichloroaniline (162 mg, 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, precipitated from an ethyl acetate solution by the addition of hexanes, and dried to yield 25 mg (18%) of the compound as a yellow solid.

Workup

  1. customPrecipitate formed in the reaction tube approximately 5 minutes
  2. customThe resulting solid was isolated by filtration
  3. customprecipitated from an ethyl acetate solution by the addition of hexanes
  4. customdried

Sources & evidence

ORD record
ord-9a2c9386d505447fa3ef46c1e8067d9c
Source dataset
uspto-grants-2011_01
Patent number
US07875728B2

Reaction notes

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