Phenacyl bromide → 2-(3-Hydroxypropylamino)-1-phenacylbenzimidazole hydrobromide

HRID 1683728Notes

Reaction equation

HRID 1683728 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][NH:5][C:6]1[NH:7][C:8]2[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=2[N:10]=1.[CH2:15]([Br:24])[C:16]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:17]>C(O)(C)C>[BrH:24].[OH:1][CH2:2][CH2:3][CH2:4][NH:5][C:6]1[N:7]([CH2:15][C:16]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[O:17])[C:8]2[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=2[N:10]=1

Participants

4

Reactant 2

HCID 6259Phenacyl bromideHCID 20033253-(1H-Benzimidazol-2-ylamino)-1-propanol

Product 1

HCID 190408622-(3-Hydroxypropylamino)-1-phenacylbenzimidazole hydrobromide

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

Heat at reflux for 5 to 6 hours a mixture of 1.91 g (10 mmol) of the compound obtained in Step A and 1.99 g (10 mmol) of phenacyl bromide in 20 ml of isopropanol. Cool. Collect the title compound precipitate by filtration and wash with acetone. Recrystallise from ethanol.

Workup

  1. temperatureHeat
  2. temperatureat reflux for 5 to 6 hours
  3. temperatureCool
  4. customCollect the title compound precipitate
  5. filtrationby filtration
  6. washwash with acetone
  7. customRecrystallise from ethanol

Sources & evidence

ORD record
ord-02088260d68f4bad9c14e090ca107390
Source dataset
uspto-grants-1997_06
Patent number
US05639756

Reaction notes

Loading…