Dimethyl Sulfate → 2-chloro-1-methyl-1H-1,3-benzodiazole

HRID 707437Notes

Reaction equation

HRID 707437 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.[OH-].[Na+].S(OC)(O[CH3:17])(=O)=O>>[Cl:1][C:2]1[N:6]([CH3:17])[C:5]2[CH:7]=[CH:8][CH:9]=[CH:10][C:4]=2[N:3]=1

Participants

4

Reactant 3

HCID 6497Dimethyl SulfateHCID 14798Sodium HydroxideHCID 785722-Chlorobenzimidazole

Product 1

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

Procedure

To a solution of 2-chloro-1H-benzo[d]imidazole (3.0019 g, 19.67 mmol, Sigma-Aldrich Chemical Company, Inc.) in 2.5 M sodium hydroxide solution (19.67 ml, 49.2 mmol, J. T. Baker) at 0° C. was added dimethyl sulfate (3.01 ml, 31.5 mmol, Riedel de Haen AG) dropwise. The reaction was allowed to stir for 1½ h. White precipitate was noted to form. The white precipitate was filtered, washed with water, and dried to give the title compound. LCMS showed product peak at 1.47 min (m+1=167.0). 1H NMR (400 MHz, DMSO-d6) δ ppm 3.80 (s, 3 H) 7.21-7.28 (m, 1 H) 7.28-7.35 (m, 1 H) 7.59 (d, J=3.72 Hz, 1 H) 7.61 (d, J=3.72 Hz, 1 H)

Workup

  1. customto form
  2. filtrationThe white precipitate was filtered
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-50f30fc27ae8470a9823a00aeb7c960d
Source dataset
uspto-grants-2015_11
Patent number
US09174992B2

Reaction notes

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