Water → 4-(4-nitro-1H-benzimidazol-1-yl)benzonitrile

HRID 1051166Notes

Reaction equation

HRID 1051166 reaction equation
[H-].[Na+].[N+:3]([C:6]1[C:14]2[N:13]=[CH:12][NH:11][C:10]=2[CH:9]=[CH:8][CH:7]=1)([O-:5])=[O:4].F[C:16]1[CH:23]=[CH:22][C:19]([C:20]#[N:21])=[CH:18][CH:17]=1.O>CN(C=O)C>[N+:3]([C:6]1[C:14]2[N:13]=[CH:12][N:11]([C:16]3[CH:23]=[CH:22][C:19]([C:20]#[N:21])=[CH:18][CH:17]=3)[C:10]=2[CH:9]=[CH:8][CH:7]=1)([O-:5])=[O:4]

Participants

6

Reactant 4

HCID 962WaterHCID 145174-FluorobenzonitrileHCID 24758Sodium hydrideHCID 1609494-Nitrobenzimidazole

Product 1

HCID 683865734-(4-nitro-1H-benzimidazol-1-yl)benzonitrileYield 83.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred suspension of sodium hydride (665 mg, 16.64 mmol) in DMF (90 mL) at rt was added 4-nitro-1H-benzimidazole (2714 mg, 16.64 mmol) in several portions. After stirring for 1 h, 4-fluorobenzonitrile (1350 mg, 11.146 mmol) was added and the mixture was stirred for 15 h at 130° C. After cooling, water was added, the precipitate was filtered off, washed with water and dried to yield 4-(4-nitro-benzoimidazol-1-yl)-benzonitrile (2.47 g, 47.76%).

Workup

  1. stirringthe mixture was stirred for 15 h at 130° C
  2. temperatureAfter cooling
  3. filtrationthe precipitate was filtered off
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-4c94f1d08b844e3c8526e3a876c94d6e
Source dataset
uspto-grants-2016_07
Patent number
US09388140B2

Reaction notes

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