Hydrogen Bromide → 1-(3-bromopropyl)-5,6-dichloro-1,3-dihydro-2H-benzimidazol-2-one

HRID 126848Notes

Reaction equation

HRID 126848 reaction equation
[Cl:1][C:2]1[C:15]([Cl:16])=[CH:14][C:5]2[N:6]([CH2:10][CH2:11][CH2:12]O)[C:7](=[O:9])[NH:8][C:4]=2[CH:3]=1.[BrH:17]>O>[Br:17][CH2:12][CH2:11][CH2:10][N:6]1[C:5]2[CH:14]=[C:15]([Cl:16])[C:2]([Cl:1])=[CH:3][C:4]=2[NH:8][C:7]1=[O:9]

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 202880345,6-dichloro-1,3-dihydro-1-(3-hydroxypropyl)-2H-benzimidazol-2-one

Product 1

HCID 202880671-(3-bromopropyl)-5,6-dichloro-1,3-dihydro-2H-benzimidazol-2-oneYield 81%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A mixture of 57.5 parts of 5,6-dichloro-1,3-dihydro-1-(3-hydroxypropyl)-2H-benzimidazol-2-one and 450 parts of a hydrobromic acid solution 48% in water is stirred and refluxed for 2.50 hours. The reaction mixture is cooled and water is added. The precipitated product is filtered off, stirred in 700 parts of water, filtered off again and dried in vacuo, yielding 59 parts (81%) of 1-(3-bromopropyl)-5,6-dichloro-1,3-dihydro-2H-benzimidazol-2-one; mp. 198.1° C.

Workup

  1. temperaturerefluxed for 2.50 hours
  2. temperatureThe reaction mixture is cooled
  3. filtrationThe precipitated product is filtered off
  4. stirringstirred in 700 parts of water
  5. filtrationfiltered off again
  6. customdried in vacuo

Sources & evidence

ORD record
ord-af68619533ab484c9d2788f36e347762
Source dataset
uspto-grants-1981_03
Patent number
US04254127

Reaction notes

Loading…