Sulfuric Acid → 5-Bromo-1-(4-fluorophenyl)-3-methyl-1,3-dihydro-benzimidazol-2-one

HRID 244464Notes

Reaction equation

HRID 244464 reaction equation
[Br:1][C:2]1[CH:18]=[CH:17][C:5]2[N:6]([C:10]3[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=3)[C:7](=[O:9])[NH:8][C:4]=2[CH:3]=1.[CH3:19][Si]([N-][Si](C)(C)C)(C)C.[Li+].CI.S(=O)(=O)(O)O>COCCOCCOC>[Br:1][C:2]1[CH:18]=[CH:17][C:5]2[N:6]([C:10]3[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=3)[C:7](=[O:9])[N:8]([CH3:19])[C:4]=2[CH:3]=1

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 6328Methyl iodideHCID 2733832Lithium HexamethyldisilazideHCID 594372015-Bromo-1-(4-fluorophenyl)-1,3-dihydrobenzimidazol-2-one

Product 1

HCID 594372865-Bromo-1-(4-fluorophenyl)-3-methyl-1,3-dihydro-benzimidazol-2-oneYield 95.8%

Reagents, catalysts & solvents 1

HCID 8150DiglymeSolvent

Procedure

To a stirred room temperature suspension of 5-bromo-1-(4-fluorophenyl)-1,3-dihydro-benzimidazol-2-one (160 mg, 0.52 mmol) in anhydrous bis(2-methoxyethyl)ether (5 mL) was added lithium bis(trimethylsilyl)amide (0.55 mL of 1.06 M solution in THF, 0.58 mmol). After 30 minutes, methyl iodide (125 μL, 2 mmol) was added. After 2 hours, the mixture was poured into 1 N sulfuric acid containing ice. The resulting precipitate was filtered, washed with water, and dried to afford 160 mg of 5-bromo-1-(4-fluorophenyl)-3-methyl-1,3-dihydro-benzimidazol-2-one as an off-white solid. MS m/z 321/323 (MH+).

Workup

  1. waitAfter 2 hours
  2. additioncontaining ice
  3. filtrationThe resulting precipitate was filtered
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-104da1b2cfac47e9a104beb41d3c2052
Source dataset
uspto-grants-2014_02
Patent number
US08658637B2

Reaction notes

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