Dimethylformamide → HCID 14800486, compound

HRID 704330Notes

Reaction equation

HRID 704330 reaction equation
CN(C)C=O.[H-].[Na+].[F: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.[F:19][C:20]([F:41])([F:40])[S:21]([O:24][C:25]1[CH:39]=[CH:38][C:28]([O:29][C:30]2[CH:37]=[CH:36][C:33]([CH2:34]Br)=[CH:32][CH:31]=2)=[CH:27][CH:26]=1)(=[O:23])=[O:22]>O>[F:8][C:9]1[C:17]2[N:16]=[C:15]([CH3:18])[N:14]([CH2:34][C:33]3[CH:32]=[CH:31][C:30]([O:29][C:28]4[CH:27]=[CH:26][C:25]([O:24][S:21]([C:20]([F:41])([F:19])[F:40])(=[O:23])=[O:22])=[CH:39][CH:38]=4)=[CH:37][CH:36]=3)[C:13]=2[CH:12]=[CH:11][CH:10]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 14800485HCID 14800485, compoundHCID 178432156HCID 178432156, compound

Product 1

HCID 14800486HCID 14800486, compoundYield 46.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of anhydrous N,N-dimethylformamide (10 ml) and sodium hydride (60% oil suspension; 29 mg), 4-fluoro-2-methylbenzimidazole (110 mg) was added while stirring, and stirring was continued at room temperature for 1 hour. To the reaction mixture, a solution of 4-(4-trifluoromethylsulfonyloxyphenoxy)benzyl bromide (300 mg) in anhydrous N,N-dimethylformaide (3 ml) was dropwise added, followed by stirring at room temperature for 5 hours. 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 eliminate toluene The residue was purified by silica gel column chromatography to give 4-fluoro-2-methyl-1-[4-(4-trifluoromethylsulfonyloxyphenoxy)benzyl]benzimidazole (164 mg) as a colorless liquid nD26 1.5615.

Workup

  1. additionwas added
  2. stirringstirring
  3. stirringby stirring at room temperature for 5 hours
  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. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-0e1e98d747d949dc8bba78928bc777e4
Source dataset
uspto-grants-1991_01
Patent number
US04987145

Reaction notes

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