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

HRID 1621017Notes

Reaction equation

HRID 1621017 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>[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

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 785722-Chlorobenzimidazole

Product 1

HCID 6630802-chloro-1-methyl-1H-1,3-benzodiazoleYield 67.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 2-chloro-1H-benzo[d]imidazole (2.0 g, 13.1 mmol) in DMF (10 mL) was added NaH (0.63 g, 15.7 mmol) at 0° C. under N2. After stirring for 30 min at 0° C., iodomethane (5.58 g, 39.3 mmol) was added and the mixture was stirred at room temperature for additional 1 hour. The reaction mixture was quenched with water (100 mL). The aqueous layer was extracted with EtOAc (3×20 mL). The combined organic layers were dried over Na2SO4, filtered, and concentrated to give the title compound (1.9 mg, 8.9 mmol, 67.9% yield) as a white solid. MS: MS (M+H)+; 1H NMR (400 MHz, CDCl3): δ 7.71-7.68 (m, 1H), 7.31-7.27 (m, 3H), 3.79 (s, 3H).

Workup

  1. stirringthe mixture was stirred at room temperature for additional 1 hour
  2. customThe reaction mixture was quenched with water (100 mL)
  3. extractionThe aqueous layer was extracted with EtOAc (3×20 mL)
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-4600554775b44dcdb291fb2c8b467822
Source dataset
uspto-grants-2014_07
Patent number
US08772500B2

Reaction notes

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