Imidazole → 5-(1-Imidazolyl)-2-nitrobenzonitrile

HRID 618667

Reaction equation

HRID 618667 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]([N+:10]([O-:12])=[O:11])=[C:6]([CH:9]=1)[C:7]#[N:8].[NH:13]1[CH:17]=[CH:16][N:15]=[CH:14]1>CC(N(C)C)=O>[N:13]1([C:2]2[CH:3]=[CH:4][C:5]([N+:10]([O-:12])=[O:11])=[C:6]([CH:9]=2)[C:7]#[N:8])[CH:17]=[CH:16][N:15]=[CH:14]1

Participants

4

Reactant 2

HCID 795ImidazoleHCID 1005065-Chloro-2-nitrobenzonitrile

Product 1

HCID 218478205-(1-Imidazolyl)-2-nitrobenzonitrileYield 107.8%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 5-chloro-2-nitrobenzonitrile (20.0 g) and imidazole (22.3 g) in DMA (150 ml) was heated at 140° C. for 6 hours. The mixture was evaporated and the residue was triturated with water to give 5-(1-imidazolyl)-2-nitrobenzonitrile (25.3 g); NMR Spectrum: (CD3SOCD3) 7.20 (d, 1H), 8.05 (t, 1H), 8.28 (m, 1H), 8.62 (m, 2H), 8.51 (d, 1H);

Workup

  1. customThe mixture was evaporated
  2. customthe residue was triturated with water

Sources & evidence

ORD record
ord-d929b6519f5a4617a4c00bf24f28fa1a
Source dataset
uspto-grants-1999_09
Patent number
US05955464

Linked notes

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