Phosgene → 1-Acetyl-7-bromo-1,3-dihydro-2H-benzimidazol-2-one

HRID 1270400Notes

Reaction equation

HRID 1270400 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Br:8])[C:3]=1[NH:9][C:10](=[O:12])[CH3:11].[C:13](Cl)(Cl)=[O:14]>C(#N)C>[C:10]([N:9]1[C:3]2[C:4]([Br:8])=[CH:5][CH:6]=[CH:7][C:2]=2[NH:1][C:13]1=[O:14])(=[O:12])[CH3:11]

Participants

4

Reactant 2

HCID 6371PhosgeneHCID 18449402N-(2-Amino-6-bromophenyl)acetamide

Product 1

HCID 184493611-Acetyl-7-bromo-1,3-dihydro-2H-benzimidazol-2-one

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of N-(2-amino-6-bromophenyl)acetamide from Step A (3.5 g, 15.28 mmol) in acetonitrile (100 mL) was added phosgene (1.9 M in toluene, 8 mL, 15.2 mmol). After 10 min, the mixture was concentrated, redissolved in water, and the solid was collected by filtration, washed with H2O and dried in vacuo to give the title compound. MS: m/z=256 (M+1).

Workup

  1. concentrationthe mixture was concentrated
  2. dissolutionredissolved in water
  3. filtrationthe solid was collected by filtration
  4. washwashed with H2O
  5. customdried in vacuo

Sources & evidence

ORD record
ord-4f72808b60234f7881000b4684d47d57
Source dataset
uspto-grants-2007_04
Patent number
US07202251B2

Reaction notes

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