Water → 4-Bromo-6-chloro-1-methyl-1H-benzo[d]imidazole

HRID 1024042Notes

Reaction equation

HRID 1024042 reaction equation
[Br:1][C:2]1[C:10]2[N:9]=[CH:8][NH:7][C:6]=2[CH:5]=[C:4]([Cl:11])[CH:3]=1.[C:12](=O)([O-])[O-].[K+].[K+].IC.O>CN(C)C=O>[Br:1][C:2]1[C:10]2[N:9]=[CH:8][N:7]([CH3:12])[C:6]=2[CH:5]=[C:4]([Cl:11])[CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 866841377-Bromo-5-chloro-1H-benzimidazole

Product 1

HCID 866841384-Bromo-6-chloro-1-methyl-1H-benzo[d]imidazoleYield 38%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 109c (3.5 g, 15 mmol) in N,N-dimethylformamide (30 mL) was added potassium carbonate (4.14 g, 30 mmol) and iodomethane (1.4 mL, 22.7 mmol). The reaction was stirred at room temperature for overnight. Water (50 mL) was added to quench the reaction and the resulting mixture was extracted with ethyl acetate (5 mL×3). The combined organic phase was dried over anhydrous Na2SO4, filtered, and evaporated under reduced pressure. The residue was purified by column chromatography eluting with petroleum ether/ethyl acetate (from 4:1 to 1:2) to afford 109d as a white solid (1.4 g, 38%). LCMS: [M+H]+ 245/247. 1H NMR (500 MHz, CDCl3) δ 7.89 (s, 1H), 7.46 (d, J=2.0 Hz, 1H), 7.32 (d, J=2.0 Hz, 1H), 3.81 (s, 3H).

Workup

  1. customto quench
  2. customthe reaction
  3. extractionthe resulting mixture was extracted with ethyl acetate (5 mL×3)
  4. dry with materialThe combined organic phase was dried over anhydrous Na2SO4
  5. filtrationfiltered
  6. customevaporated under reduced pressure
  7. customThe residue was purified by column chromatography
  8. washeluting with petroleum ether/ethyl acetate (from 4:1 to 1:2)

Sources & evidence

ORD record
ord-553315657c694829a329b6c4009c7049
Source dataset
uspto-grants-2014_05
Patent number
US08722676B2

Reaction notes

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