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

HRID 1886037Notes

Reaction equation

HRID 1886037 reaction equation
[Cl:1][C:2]1[NH:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1.[H-].[Na+].[CH3:13]I>CN(C=O)C>[Cl:1][C:2]1[N:6]([CH3:13])[C:5]2[CH:7]=[CH:8][CH:9]=[CH:10][C:4]=2[N:3]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 785722-Chlorobenzimidazole

Product 1

HCID 6630802-chloro-1-methyl-1H-1,3-benzodiazoleYield 71%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
5 °C

Procedure

According to the procedure D. Harrison, et al., J. Chem. Soc., 2930, 1963, to a cooled (5° C.), stirred solution of 2-chlorobenzimidazole (26.1 g, 0.171 mol) in DMF (125 mL) was added NaH (60% dispersion in mineral oil; 7.2 g, 0.180 mol) in several portions. After 30 minutes MeI (25.5 g, 0.180 mol) was added. The cooling bath was removed and stirring was continued for 30 minutes. The mixture was recooled, H2O (200 mL) was added, and the resulting precipitate was collected by filtration to give 20.2 g (71%) of product as an off-white solid m.p. 107°-109° C.

Workup

  1. customThe cooling bath was removed
  2. additionH2O (200 mL) was added
  3. filtrationthe resulting precipitate was collected by filtration

Sources & evidence

ORD record
ord-4e6700a876e34540831cd2db9dd7d849
Source dataset
uspto-grants-1992_09
Patent number
US05149700

Reaction notes

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