Water → 2-chloro-1-methyl-1H-1,3-benzodiazole

HRID 1791933Notes

Reaction equation

HRID 1791933 reaction equation
[H-].[Na+].[Cl:3][C:4]1[NH:5][C:6]2[CH:12]=[CH:11][CH:10]=[CH:9][C:7]=2[N:8]=1.[CH3:13]I.O>CN(C=O)C>[Cl:3][C:4]1[N:8]([CH3:13])[C:7]2[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=2[N:5]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 785722-Chlorobenzimidazole

Product 1

HCID 6630802-chloro-1-methyl-1H-1,3-benzodiazole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (contained by 60%, 0.288 g) was suspended in DMF (10 mL), and 2-chlorobenzimidazole (1 g) was added thereto. The mixture was stirred at room temperature for 30 min and methyl iodide (0.61 mL) was added thereto. After stirring at room temperature for 1 hr, water was added to the reaction mixture. The mixture was extracted with ethyl acetate, and the extract was washed with brine and concentrated under reduced pressure to give 2-chloro-1-methylbenzimidazole (0.928 g) as a white powder.

Workup

  1. stirringAfter stirring at room temperature for 1 hr
  2. extractionThe mixture was extracted with ethyl acetate
  3. washthe extract was washed with brine
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-5e9ba6ad0e98430d9baae746e4614fd4
Source dataset
uspto-grants-2006_07
Patent number
US07074794B2

Reaction notes

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