Dimethyl Sulfate → HCID 22153306, compound

HRID 1111094Notes

Reaction equation

HRID 1111094 reaction equation
[Br:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[NH:10][C:11]3[CH:17]=[CH:16][CH:15]=[CH:14][C:12]=3[N:13]=2)=[CH:5][CH:4]=1.[C:18](=O)(O)[O-].[Na+].COS(OC)(=O)=O>CC(C)=O>[CH3:18][N:13]1[C:12]2[CH:14]=[CH:15][CH:16]=[CH:17][C:11]=2[N:10]=[C:9]1[C:6]1[CH:7]=[CH:8][C:3]([CH2:2][Br:1])=[CH:4][CH:5]=1

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 516892Sodium BicarbonateHCID 22153307HCID 22153307, compound

Product 1

HCID 22153306HCID 22153306, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
40 °C

Procedure

To a stirred solution of 143.6 g (0.5 mole) of 2-(4-bromomethylphenyl)benzimidazole and 42.0 g (0.5 mole) of sodium bicarbonate in 85% aqueous acetone is added 66.0 g (0.5 mole) of dimethylsulfate dropwise. The mixture is stirred at 40° C. for about 3 hours until thin-layer chromatography indicates that the reaction is complete. The solvent is removed in vacuo, and the solid product is washed with water to eliminate sodium salts and purified by recrystallization from benzene.

Workup

  1. customThe solvent is removed in vacuo
  2. washthe solid product is washed with water
  3. custompurified by recrystallization from benzene

Sources & evidence

ORD record
ord-e9e20267c51b4baa8fd2cf769de88779
Source dataset
uspto-grants-1990_12
Patent number
US04978476

Reaction notes

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