Water → 2-(4-Bromophenyl)-1-phenyl-1H-benzo(d)imidazole

HRID 1479931Notes

Reaction equation

HRID 1479931 reaction equation
[C:1]1([NH:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[NH2:14])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:15][C:16]1[CH:23]=[CH:22][C:19]([CH:20]=O)=[CH:18][CH:17]=1.OOS([O-])=O.[K+].O>CN(C=O)C>[Br:15][C:16]1[CH:23]=[CH:22][C:19]([C:20]2[N:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=3[N:14]=2)=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 962WaterHCID 68297N-Phenyl-o-phenylenediamineHCID 707414-BromobenzaldehydeHCID 23707502Potassium hydroxy sulfite

Product 1

HCID 230940702-(4-Bromophenyl)-1-phenyl-1H-benzo(d)imidazoleYield 35.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
40 °C

Procedure

N-Phenyl-o-phenylenediamine (50 g, 0.27 mol) is dissolved in anhydrous DMF (400 ml) under N2, and 4-bromobenzaldehyde (45.5 g, 0.25 mol) is added dropwise. The reaction mixture is warmed to 40° C., and Oxone (potassium hydrogen monopersulfate, 98.1 g, 0.16 mol) is added in portions. After the mixture has been stirred at room temperature for 120 min., 1 l of water is added. The precipitated product is filtered off, washed with water and dried in vacuo. Recrystallisation from acetonitrile gives a cream-coloured solid (31 g, 35%).

Workup

  1. filtrationThe precipitated product is filtered off
  2. washwashed with water
  3. customdried in vacuo
  4. customRecrystallisation from acetonitrile

Sources & evidence

ORD record
ord-fdbd7cab8faf4656af51c2d3803ee7f6
Source dataset
uspto-grants-2016_08
Patent number
US09409883B2

Reaction notes

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