Potassium Iodide → 1-(4-Fluorobenzyl)-2-chlorobenzimidazole

HRID 2309611Notes

Reaction equation

HRID 2309611 reaction equation
[Cl:1][C:2]1[NH:6][C:5]2[CH:7]=[CH:8][CH:9]=[CH:10][C:4]=2[N:3]=1.Cl[CH2:12][C:13]1[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=1.C(=O)([O-])[O-].[Na+].[Na+].[I-].[K+]>O.CN(C)C=O>[Cl:1][C:2]1[N:6]([CH2:12][C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)[C:5]2[CH:7]=[CH:8][CH:9]=[CH:10][C:4]=2[N:3]=1

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 96024-Fluorobenzyl chlorideHCID 10340Sodium CarbonateHCID 785722-Chlorobenzimidazole

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 60 parts of 2-chloro-1H-benzimidazole, 58 parts of 1-(chloromethyl)-4-fluorobenzene, 42.5 parts of sodium carbonate, 0.1 parts of potassium iodide and 135 parts of N,N-dimethylformamide was stirred and heated overnight at 70° C. The reaction mixture was poured into water. The precipitated product was filtered off and dissolved in trichloromethane. The solution was dried, filtered and evaporated. The residue was crystallized from 2,2'-oxybispropane, yielding 62.5 parts of 2-chloro-1-(4-fluorophenylmethyl)-1H-benzimidazole (61).

Workup

  1. filtrationThe precipitated product was filtered off
  2. dissolutiondissolved in trichloromethane
  3. customThe solution was dried
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was crystallized from 2,2'-oxybispropane

Sources & evidence

ORD record
ord-0065b1b463ca4649a9f6000a63b333ea
Source dataset
uspto-grants-1987_09
Patent number
US04695575

Reaction notes

Loading…