Malononitrile → HCID 178436433, compound

HRID 2304416Notes

Reaction equation

HRID 2304416 reaction equation
[CH2:1]([C:3]1[CH:4]=[C:5]([NH:9][N:10]=[C:11]([C:14]#[N:15])[C:12]#[N:13])[CH:6]=[CH:7][CH:8]=1)[CH3:2].C(C1C=C(C=CC=1)N)C.C(#N)CC#N.O.[NH2:31][NH2:32]>>[NH2:13][C:12]1[C:11](=[N:10][NH:9][C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([CH2:1][CH3:2])[CH:4]=2)[C:14]([NH2:15])=[N:32][N:31]=1

Participants

5

Reactant 4

HCID 8010MalononitrileHCID 114753-EthylanilineHCID 24654Hydrazine hydrate (1:1)2×HCID 12051878HCID 12051878, compound

Product 1

HCID 178436433HCID 178436433, compoundYield 10%

Procedure

3,5-Diamino-4-[(3-ethylphenyl)hydrazono]pyrazole was prepared using 99 mg (0.5 mmol) of 2-[(3-ethylphenyl)hydrazono]malononitrile, which was derived from 3-ethylaniline (124 μL, 1.0 mmol) and malononitrile (1.5 mmol) as described in Example 8, and hydrazine hydrate. Precipitate formed in the reaction tube approximately 10 min 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 12 mg (10%) of the title compound as a yellow solid.

Workup

  1. custom3,5-Diamino-4-[(3-ethylphenyl)hydrazono]pyrazole was prepared
  2. customPrecipitate formed in the reaction tube approximately 10 min
  3. customThe resulting solid was isolated by filtration
  4. customprecipitated from an ethyl acetate solution by the addition of hexanes
  5. customdried

Sources & evidence

ORD record
ord-e5a7a7ed73ca49b082764630e91b58f0
Source dataset
uspto-grants-2002_08
Patent number
US06436915B1

Reaction notes

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