Dimethyl Sulfate → 2-(2-Bromophenyl)-1-methyl-1H-benzimidazole

HRID 1471228Notes

Reaction equation

HRID 1471228 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[NH:12][C:11]2[CH:13]=[CH:14][CH:15]=[CH:16][C:10]=2[N:9]=1.[H-].[Na+].[CH3:19]OS(OC)(=O)=O>O1CCCC1>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:9]([CH3:19])[C:10]2[CH:16]=[CH:15][CH:14]=[CH:13][C:11]=2[N:12]=1

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 24758Sodium hydrideHCID 975112-(2-Bromophenyl)-1H-benzimidazole

Product 1

HCID 160848932-(2-Bromophenyl)-1-methyl-1H-benzimidazoleYield 83.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a flask were added 3.3 g 2-(2-bromophenyl)-1H-benzimidazole and 100 ml tetrahydrofuran and the mixture was cooled to 10 C under nitrogen. 0.63 g Sodium hydride were added in portions and the reaction mixture was stirred for 20 minutes. 2.0 g Dimethylsulfate were added and the mixture was heated to 22 C for 30 minutes. The mixture was quenched slowly with 100 ml water, extracted with ethyl acetate and then extracted into a 1M hydrochloric acid solution. The solution was washed with ethyl acetate and then basified with 3M sodium hydroxide. Following extraction with ethyl acetate and solvent removal, the solid was dissolved in a hot mixture of 20 ml hexane with 4 ml 2-propanol. After cooling to 5 C, the product was filtered, washed with hexane and dried giving 2.9 g of a white solid.

Workup

  1. temperaturethe mixture was cooled to 10 C under nitrogen
  2. temperaturethe mixture was heated to 22 C for 30 minutes
  3. customThe mixture was quenched slowly with 100 ml water
  4. extractionextracted with ethyl acetate
  5. extractionextracted into a 1M hydrochloric acid solution
  6. washThe solution was washed with ethyl acetate
  7. extractionextraction
  8. customwith ethyl acetate and solvent removal
  9. dissolutionthe solid was dissolved in a hot mixture of 20 ml hexane with 4 ml 2-propanol
  10. temperatureAfter cooling to 5 C
  11. filtrationthe product was filtered
  12. washwashed with hexane
  13. customdried

Sources & evidence

ORD record
ord-7bbe9fbfaea1405b97468a3c545a1fa8
Source dataset
uspto-grants-2015_04
Patent number
US09011734B2

Reaction notes

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