Imidazole → 4-Amino-2-(1-imidazolyl)-5-nitrobenzonitrile

HRID 1974479Notes

Reaction equation

HRID 1974479 reaction equation
[NH2:1][C:2]1[C:9]([N+:10]([O-:12])=[O:11])=[CH:8][C:5]([C:6]#[N:7])=[C:4](F)[CH:3]=1.[NH:14]1[CH:18]=[CH:17][N:16]=[CH:15]1>CN(C=O)C.O>[NH2:1][C:2]1[C:9]([N+:10]([O-:12])=[O:11])=[CH:8][C:5]([C:6]#[N:7])=[C:4]([N:14]2[CH:18]=[CH:17][N:16]=[CH:15]2)[CH:3]=1

Participants

5

Reactant 2

HCID 795ImidazoleHCID 104197934-Amino-2-fluoro-5-nitrobenzonitrile

Product 1

HCID 104437844-Amino-2-(1-imidazolyl)-5-nitrobenzonitrileYield 94.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

In 5 ml of DMF were dissolved 1 g of 4-amino-2-fluoro-5-nitrobenzonitrile and 1.1 g of imidazole, and the mixture was stirred at 100° C. for 1 hour. The reaction mixture was then diluted with water and the resulting crystals were recovered by filtration to provide 1.2 g of 4-amino-2-(1-imidazolyl)-5-nitrobenzonitrile. Physicochemical properties:

Workup

  1. filtrationthe resulting crystals were recovered by filtration

Sources & evidence

ORD record
ord-e22b3da583c34e09ab26d9a16d00bdb4
Source dataset
uspto-grants-1994_02
Patent number
US05283244

Reaction notes

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