4-Fluorobenzyl chloride → 1-(4-Fluorobenzyl)-2-chlorobenzimidazole

HRID 2210827Notes

Reaction equation

HRID 2210827 reaction equation
[Cl:1][C:2]1[NH:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1.[F:11][C:12]1[CH:19]=[CH:18][C:15]([CH2:16]Cl)=[CH:14][CH:13]=1>O.[OH-].[Na+]>[Cl:1][C:2]1[N:6]([CH2:16][C:15]2[CH:18]=[CH:19][C:12]([F:11])=[CH:13][CH:14]=2)[C:5]2[CH:7]=[CH:8][CH:9]=[CH:10][C:4]=2[N:3]=1

Participants

5

Reactant 2

HCID 96024-Fluorobenzyl chlorideHCID 785722-Chlorobenzimidazole

Product 1

HCID 30202411-(4-Fluorobenzyl)-2-chlorobenzimidazole

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
82 °C

Procedure

11 g 2-chlorobenzimidazole are dissolved in 74 ml water and 17.35 ml 30% sodium hydroxide. The mixture is heated to 82° C. and to this they are slowly added 23.76 g 4-fluorobenzyl chloride within 5 hours. When the reaction is achieved, the solution is cooled to 20° C. and extracted with methylene chloride. The compound is recrystallized from ethyl acetate.

Workup

  1. customwithin 5 hours
  2. temperaturethe solution is cooled to 20° C.
  3. extractionextracted with methylene chloride
  4. customThe compound is recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-38be100858744f36812033d926cbc878
Source dataset
uspto-grants-1995_10
Patent number
US05461059

Reaction notes

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