Methyl iodide → HCID 69134405, compound

HRID 969525Notes

Reaction equation

HRID 969525 reaction equation
[CH2:1]([O:8][C:9]1[C:17]2[N:16]=[C:15]([C:18]([F:21])([F:20])[F:19])[NH:14][C:13]=2[CH:12]=[C:11]([Br:22])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:23](=O)([O-])[O-].[K+].[K+].CI>CC(C)=O>[CH2:1]([O:8][C:9]1[C:17]2[N:16]=[C:15]([C:18]([F:21])([F:19])[F:20])[N:14]([CH3:23])[C:13]=2[CH:12]=[C:11]([Br:22])[CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 69135137HCID 69135137, compound

Product 1

HCID 69134405HCID 69134405, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 40 g (107.8 mmol) 4-benzyloxy-6-bromo-2-trifluoromethyl-1H-benzimidazole in acetone (600 ml) was treated with 44.7 g (323.4 mmol) potassium carbonate and the reaction was refluxed for 1 h. 13.4 ml Methyl iodide were added and the mixture was stirred for 2 h. After cooling to room temperature, the precipitate was filtered off and the filtrate was concentrated in vacuo. Purification of the residue by column chromatography on silica gel (petroleum ether/ethyl acetate=15:1) afforded 13.2 g (32%) of the title compound as a white solid. m.p. 141°-142° C.

Workup

  1. temperaturethe reaction was refluxed for 1 h
  2. filtrationthe precipitate was filtered off
  3. concentrationthe filtrate was concentrated in vacuo
  4. customPurification of the residue by column chromatography on silica gel (petroleum ether/ethyl acetate=15:1)

Sources & evidence

ORD record
ord-23836f6ed0ae47b180293721ea055f22
Source dataset
uspto-grants-2007_12
Patent number
US07307084B2

Reaction notes

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