Dimethylformamide → 4-Chloro-1-[4-(4-ethoxyphenoxy)benzyl]-2-methylbenzimidazole

HRID 978039Notes

Reaction equation

HRID 978039 reaction equation
CN(C)C=O.[H-].[Na+].[Cl:8][C:9]1[C:17]2[NH:16][C:15]([CH3:18])=[N:14][C:13]=2[CH:12]=[CH:11][CH:10]=1.[CH2:19]([O:21][C:22]1[CH:36]=[CH:35][C:25]([O:26][C:27]2[CH:34]=[CH:33][C:30]([CH2:31]Cl)=[CH:29][CH:28]=2)=[CH:24][CH:23]=1)[CH3:20]>O>[Cl:8][C:9]1[C:17]2[N:16]=[C:15]([CH3:18])[N:14]([CH2:31][C:30]3[CH:33]=[CH:34][C:27]([O:26][C:25]4[CH:35]=[CH:36][C:22]([O:21][CH2:19][CH3:20])=[CH:23][CH:24]=4)=[CH:28][CH:29]=3)[C:13]=2[CH:12]=[CH:11][CH:10]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 137303804-(4-Ethoxyphenoxy)benzyl chlorideHCID 178432150HCID 178432150, compound

Product 1

HCID 137303814-Chloro-1-[4-(4-ethoxyphenoxy)benzyl]-2-methylbenzimidazoleYield 34.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of anhydrous N,N-dimethylforamide (10 ml) and sodium hydride (62% oil suspension; 0.071 g), 4-chloro-2-methylbenzimidazole (0.304 g) was added while stirring, and the stirring was continued at room temperature for 1 hour. The resultant mixture was cooled to 5°-10° C., and a solution of 4-(4-ethoxyphenoxy)benzyl chloride (0.400 g) in anhydrous N,N-dimethylformaide (10 ml) was dropwise added thereto in 30 minutes, followed by stirring at room temperature overnight. After completion of the reaction, the reaction mixture was poured into water (100 ml) and extracted with toluene (30 ml) two times. The toluene extract was washed with water, dried over anhydrous sodium sulfate and distilled under reduced pressure to remove toluene. The residue was purified by silica gel column chromatography to give 4-chloro-1-[4-(4-ethoxyphenoxy)benzyl]-2-methylbenzimidazole (0.204 g) as a colorless liquid. nD26.5 1.6087.

Workup

  1. additionwas added
  2. waitin 30 minutes
  3. stirringby stirring at room temperature overnight
  4. customAfter completion of the reaction
  5. extractionextracted with toluene (30 ml) two times
  6. extractionThe toluene extract
  7. washwas washed with water
  8. dry with materialdried over anhydrous sodium sulfate
  9. distillationdistilled under reduced pressure
  10. customto remove toluene
  11. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-c19943473bb44129a190c8b13b394e5d
Source dataset
uspto-grants-1987_05
Patent number
US04663339

Reaction notes

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