Malononitrile → HCID 178462456, compound

HRID 254974

Reaction equation

HRID 254974 reaction equation
C(N1C2C=CC(N[N:17]=[C:18]([C:21]#[N:22])[C:19]#[N:20])=CC=2C2C1=CC=CC=2)C.[NH2:23][C:24]1[CH:25]=[CH:26][C:27]2[N:28]([CH2:37][CH3:38])[C:29]3[C:34]([C:35]=2[CH:36]=1)=[CH:33][CH:32]=[CH:31][CH:30]=3.C(#N)CC#N.O.[NH2:45][NH2:46]>>[CH2:37]([N:28]1[C:27]2[CH:26]=[CH:25][C:24]([NH:23][N:17]=[C:18]3[C:19]([NH2:20])=[N:46][N:45]=[C:21]3[NH2:22])=[CH:36][C:35]=2[C:34]2[C:29]1=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH3:38]

Participants

5

Reactant 4

HCID 8010MalononitrileHCID 85883-Amino-9-ethylcarbazoleHCID 24654Hydrazine hydrate (1:1)HCID 21954985HCID 21954985, compound

Product 1

HCID 178462456HCID 178462456, compound

Procedure

4-[(9-ethyl-9H-carbazol-3-yl)hydrazono]-4H-pyrazole-3,5-diamine was prepared using 143 mg (0.5 mmol) of 2-[(9-ethyl-9H-carbazol-3-yl)hydrazono]malononitrile, which was derived from 3-amino-9-ethylcarbazole (210 mg, 1.0 mmol) and malononitrile (1.5 mmol), and hydrazine hydrate. Solids had not 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 (29%) of the compound as a black solid.

Workup

  1. customSolids had not 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-59ab560972fa4ac98075c2f4e9c5a886
Source dataset
uspto-grants-2011_01
Patent number
US07875728B2

Linked notes

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