Dimethyl Sulfate → 6-broMo-1-Methyl-1H-benzo[d]iMidazol-2(3H)-one

HRID 598889Notes

Reaction equation

HRID 598889 reaction equation
[Br:1][C:2]1[CH:18]=[CH:17][C:5]2[N:6](C(OC(C)(C)C)=O)[C:7](=O)[NH:8][C:4]=2[CH:3]=1.[C:19](=[O:22])([O-])[O-].[Na+].[Na+].S(OC)(OC)(=O)=O>C1COCC1>[Br:1][C:2]1[CH:18]=[CH:17][C:5]2[NH:6][C:19](=[O:22])[N:8]([CH3:7])[C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 10340Sodium CarbonateHCID 9796827HCID 9796827, compound

Product 1

HCID 98159826-broMo-1-Methyl-1H-benzo[d]iMidazol-2(3H)-oneYield 100.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

tert-Butyl 5-bromo-2-oxo-2,3-dihydrobenzo[d]imidazole-1-carboxylate (12 g, 38 mmol) (Puwen Zhang, et. al., Bioorganic & Medicinal Chemistry Letters 11 (2001) 2747-2750 hereby incorporated by reference) and anhydrous disodium carbonate (3.2 mL, 77 mmol) were mixed in 200 mL THF. To this mixture was added dimethyl sulfate (15 mL, 153 mmol). The mixture was stirred at room temperature for 18 hours. The solvent was evaporated. The residue was dissolved in EtOAc and washed with brine and dried over sodium sulfate. The solvent was evaporated. The residue was taken up in MeOH (50 mL) and allowed to stand 18 hours. The solvent was evaporated, and the residue was triturated from MeOH (25 mL) to provide the product as a white solid (8.7 g, 100%). LCMS (API-ES) m/z: 227, 229 (M+H+).

Workup

  1. customThe solvent was evaporated
  2. dissolutionThe residue was dissolved in EtOAc
  3. washwashed with brine
  4. dry with materialdried over sodium sulfate
  5. customThe solvent was evaporated
  6. waitto stand 18 hours
  7. customThe solvent was evaporated
  8. customthe residue was triturated from MeOH (25 mL)

Sources & evidence

ORD record
ord-5afa5eb1069e4c9e90c201afd9040c6d
Source dataset
uspto-grants-2011_03
Patent number
US07897619B2

Reaction notes

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