Water → 25699-95-0

HRID 1959995Notes

Reaction equation

HRID 1959995 reaction equation
[H-].[Na+].[N:3]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[NH:5][CH:4]=1.Cl[C:13]1[CH:20]=[CH:19][C:16]([C:17]#[N:18])=[CH:15][CH:14]=1.O>CN(C)C=O>[C:17]([C:16]1[CH:19]=[CH:20][C:13]([N:3]2[C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=3[N:5]=[CH:4]2)=[CH:14][CH:15]=1)#[N:18]

Participants

6

Reactant 4

HCID 962WaterHCID 5798BenzimidazoleHCID 121634-ChlorobenzonitrileHCID 24758Sodium hydride

Product 1

HCID 532845425699-95-0

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
130 °C

Procedure

Sodium hydride (60% strength in mineral oil; 24.0 g, 0.60 mol) is placed in a flask and admixed with N,N-dimethylformamide (80 ml). A solution of benzimidazole (73.3 g, 0.60 mol) in N,N-dimethylformamide (250 ml) is added dropwise to the suspension over a period of 1 hour. After H2 evolution has ceased 4-chlorobenzonitrile (55.6 g, 0.40 mol) is added and the mixture is subsequently heated at 130° C. for 10.5 hours. After cooling to room temperature, the reaction mixture is poured into water (4 I) and the residue formed is filtered off with suction, washed with water and dried under reduced pressure. This gives 90.6 g of 1-(4-cyanophenyl)benzimidazole which still comprises mineral oil as contaminant.

Workup

  1. additionis added
  2. temperatureAfter cooling to room temperature
  3. customthe residue formed
  4. filtrationis filtered off with suction
  5. washwashed with water
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-cf5bae4b3f0847d68309ebda888ec5b4
Source dataset
uspto-grants-2013_04
Patent number
US08410280B2

Reaction notes

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