Malononitrile → HCID 178492413, compound

HRID 2095134Notes

Reaction equation

HRID 2095134 reaction equation
COC1C=C(N[N:12]=[C:13]([C:16]#[N:17])[C:14]#[N:15])C=CC=1OC.[NH2:18][C:19]1[CH:20]=[C:21]([O:27][CH3:28])[C:22]([O:25][CH3:26])=[CH:23][CH:24]=1.C(#N)CC#N.O.[NH2:35][NH2:36]>>[CH3:28][O:27][C:21]1[CH:20]=[C:19]([NH:18][N:12]=[C:13]2[C:14]([NH2:15])=[N:36][N:35]=[C:16]2[NH2:17])[CH:24]=[CH:23][C:22]=1[O:25][CH3:26]

Participants

5

Reactant 4

HCID 8010MalononitrileHCID 227703,4-DimethoxyanilineHCID 24654Hydrazine hydrate (1:1)2×HCID 21955015HCID 21955015, compound

Product 1

HCID 178492413HCID 178492413, compound

Procedure

4-[(3,4-dimethoxyphenyl)hydrazono]-4H-pyrazole-3,5-diamine was prepared using 115 mg (0.5 mmol) of 2-[(3,4-dimethoxyphenyl)hydrazono]malononitrile, which was derived from 4-aminoveratrole (153 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. Very little solid had formed after heating the reaction at 75° C. for 1 hr, however, analysis of the reaction solution by TLC indicated that no starting material remained. The solution was allowed to cool to ambient temperature and the solvent was evaporated. The residue was dissolved in ethyl acetate and then precipitated by the addition of hexanes. The resulting solid was isolated by filtration and dried to yield 46 mg (35%) of the compound as a mustard coloured solid.

Workup

  1. dissolutionhad not fully dissolved
  2. customVery little solid had formed
  3. temperatureafter heating
  4. customthe reaction at 75° C. for 1 hr
  5. customthe solvent was evaporated
  6. dissolutionThe residue was dissolved in ethyl acetate
  7. customprecipitated by the addition of hexanes
  8. customThe resulting solid was isolated by filtration
  9. customdried

Sources & evidence

ORD record
ord-8fbcf690e22f4f08ae9a8985ed373efe
Source dataset
uspto-grants-2013_05
Patent number
US08445694B2

Reaction notes

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