Malononitrile → HCID 178509174, compound

HRID 2304426Notes

Reaction equation

HRID 2304426 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][N:9]=[C:10]([C:13]#[N:14])[C:11]#[N:12].BrC1C=CC=CC=1N.C(#N)CC#N.O.[NH2:29][NH2:30]>>[NH2:14][C:13]1[C:10](=[N:9][NH:8][C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[Br:1])[C:11]([NH2:12])=[N:30][N:29]=1

Participants

5

Reactant 4

HCID 8010MalononitrileHCID 119922-BromoanilineHCID 24654Hydrazine hydrate (1:1)HCID 779795Propanedinitrile, [(2-bromophenyl)hydrazono]-

Product 1

HCID 178509174HCID 178509174, compoundYield 73%

Procedure

This compound was prepared using 125 mg (0.5 mmol) of 2-[(2-bromophenyl)-hydrazono]malononitrile, which was derived from 2-bromoaniline (172 mg, 1.0 mmol) and malononitrile (1.5 mmol) as described in Example 8, 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 room 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 102 mg (73%) of the title compound as an orange solid.

Workup

  1. customThis compound was prepared
  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-b418cf4d719d4579a5bb2c677c7d1b3d
Source dataset
uspto-grants-2002_08
Patent number
US06436915B1

Reaction notes

Loading…