p-Toluidine → HCID 178424384, compound

HRID 254960Notes

Reaction equation

HRID 254960 reaction equation
C1(C)C=CC=CC=1[NH:7][N:8]=[C:9]([C:12]#[N:13])[C:10]#[N:11].N[C:16]1[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=1.C(#N)CC#N.O.[NH2:29][NH2:30]>>[C:19]1([CH3:22])[CH:20]=[CH:21][CH:16]=[CH:17][C:18]=1[NH:7][N:8]=[C:9]1[C:10]([NH2:11])=[N:30][N:29]=[C:12]1[NH2:13]

Participants

5

Reactant 4

HCID 7813p-ToluidineHCID 8010MalononitrileHCID 24654Hydrazine hydrate (1:1)HCID 12450559CARBONYLCYANIDE2METHYLPHENYLHYDRAZONE

Product 1

HCID 178424384HCID 178424384, compound

Procedure

4-(o-tolylhydrazono)-4H-pyrazole-3,5-diamine was prepared using 92 mg (0.5 mmol) of 2-(o-tolylhydrazono)-malononitrile, which was derived from 4-toluidine (107 μL, 1.0 mmol) and malononitrile (1.5 mmol), and hydrazine hydrate. 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 43 mg (40%) of the compound as a yellow solid.

Workup

  1. customVery little solid had formed
  2. temperatureafter heating
  3. customthe reaction at 75° C. for 1 hr
  4. customthe solvent was evaporated
  5. dissolutionThe residue was dissolved in ethyl acetate
  6. customprecipitated by the addition of hexanes
  7. customThe resulting solid was isolated by filtration
  8. customdried

Sources & evidence

ORD record
ord-6a70b60cf70c4fa887085f6d31139810
Source dataset
uspto-grants-2011_01
Patent number
US07875728B2

Reaction notes

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