Methyl iodide → 2-chloro-1-methyl-1H-1,3-benzodiazole

HRID 885447Notes

Reaction equation

HRID 885447 reaction equation
[Cl:1][C:2]1[NH:6][C:5]2[CH:7]=[CH:8][CH:9]=[CH:10][C:4]=2[N:3]=1.[H-].[Na+].I[CH3:14]>CN(C=O)C.O>[Cl:1][C:2]1[N:6]([CH3:14])[C:5]2[CH:7]=[CH:8][CH:9]=[CH:10][C:4]=2[N:3]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 785722-Chlorobenzimidazole

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-chloro-1H-benzimidazole (5.03 g, 33.0 mmol) in anhydrous DMF (33 mL) at 0° C. was added portion-wise 95% NaH (871 mg, 36.3 mmol). The ice bath was removed and the resulting mixture was stirred at room temperature for 1 h. Iodomethane (4.68 g, 33.0 mmol) was added and the resulting mixture was stirred at room temperature overnight. The resulting mixture was then diluted with water, and the resulting precipitate was collected by filtration and purified by recrystallization from hexane to yield 2-chloro-1-methyl-1H-benzimidazole. MS 167 (M+1)+

Workup

  1. customThe ice bath was removed
  2. stirringthe resulting mixture was stirred at room temperature overnight
  3. filtrationthe resulting precipitate was collected by filtration
  4. custompurified by recrystallization from hexane

Sources & evidence

ORD record
ord-c5d8004ba1ab4a7b9a1a985a1290f4a8
Source dataset
uspto-grants-2012_08
Patent number
US08242157B2

Reaction notes

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