2-Aminobenzimidazole → 1,3-dihydro-1,3-bis[2-(o-bromophenyl)ethyl]-2H-benzimidazol-2-imine hydrobromide

HRID 1415301Notes

Reaction equation

HRID 1415301 reaction equation
[NH2:1][C:2]1[NH:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1.[Br:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[CH2:18][CH2:19]Br>C1(C)C(C)=CC=CC=1>[BrH:11].[Br:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[CH2:18][CH2:19][N:3]1[C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]([CH2:19][CH2:18][C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[Br:11])[C:2]1=[NH:1]

Participants

4

Reactant 2

HCID 136242-AminobenzimidazoleHCID 3340691-Bromo-2-(2-bromoethyl)benzene

Product 1

HCID 214841691,3-dihydro-1,3-bis[2-(o-bromophenyl)ethyl]-2H-benzimidazol-2-imine hydrobromideYield 42.2%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A solution of 5.5 g of 2-aminobenzimidazole and 11.0 g of 2-(o-bromophenyl)ethyl bromide in 250 ml of xylene is heated in a nitrogen atmosphere under reflux for 18 hours. The reaction mixture is cooled and the crystals that separate are filtered and dried. This product weighs 3.7 g and is recrystallized from acetonitrile to give 3.4 g of 1,3-dihydro-1,3-bis[2-(o-bromophenyl)ethyl]-2H-benzimidazol-2-imine hydrobromide, m.p. 248°-249°.

Workup

  1. temperatureunder reflux for 18 hours
  2. temperatureThe reaction mixture is cooled
  3. customthe crystals that separate
  4. filtrationare filtered
  5. customdried
  6. customis recrystallized from acetonitrile

Sources & evidence

ORD record
ord-c71364315bbd404fb85c53266347d3ef
Source dataset
uspto-grants-1977_01
Patent number
US04004016

Reaction notes

Loading…