Sodium Hydroxide → 5-Bromo-1,3-dihydro-2H-benzimidazol-2-one

HRID 2218714Notes

Reaction equation

HRID 2218714 reaction equation
Cl[C:2](OC1C=CC=CC=1)=[O:3].[Br:11][C:12]1[CH:13]=[C:14]([NH2:19])[C:15]([NH2:18])=[CH:16][CH:17]=1.C([O-])(O)=O.[Na+].[OH-].[Na+]>CO.O>[Br:11][C:12]1[CH:17]=[CH:16][C:15]2[NH:18][C:2](=[O:3])[NH:19][C:14]=2[CH:13]=1

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 15891Phenyl chloroformateHCID 3235934-Bromobenzene-1,2-diamineHCID 516892Sodium Bicarbonate

Product 1

HCID 122280605-Bromo-1,3-dihydro-2H-benzimidazol-2-oneYield 34%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Add phenyl chloroformate (922 mg, 5.89 mmol) to a suspension of 4-bromo-benzene-1,2-diamine (1.00 g, 5.35 mmol) and NaHCO3 (483 mg, 5.89 mmol) in methanol (20 mL) and H2O (10 mL). Stir at room temperature for 3.5 h and add 1.00N aqueous NaOH (6 mL, 6.00 mmol). Stir overnight at room temperature and filter. Wash the filter cake with H2O and dry in-vacuo overnight to obtain 386 mg (34%) of the title compound as a brown powder. MS (ES) 213,215 (M+H), 211,213 (M−H); HPLC shows 95% purity.

Workup

  1. stirringStir overnight at room temperature
  2. filtrationfilter
  3. washWash the filter cake with H2O
  4. customdry in-vacuo overnight

Sources & evidence

ORD record
ord-eed0731a25984f238c7a50aa7f424136
Source dataset
uspto-grants-2008_08
Patent number
US07411072B2

Reaction notes

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