Water → HCID 19771065, compound

HRID 1589866Notes

Reaction equation

HRID 1589866 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:18]C)=[C:6]([N:8]2[C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=3[NH:10][C:9]2=[O:17])[CH:7]=1.O>Br.C(O)(=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:18])=[C:6]([N:8]2[C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=3[NH:10][C:9]2=[O:17])[CH:7]=1

Participants

5

Reactant 2

HCID 962WaterHCID 19771061HCID 19771061, compound

Product 1

HCID 19771065HCID 19771065, compoundYield 52.7%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 260Hydrogen BromideSolvent

Procedure

1-(5-chloro-2-methoxyphenyl)-1,3-dihydro-2H-benzimidazol-2-one (0.3 g) was refluxed for 32 hours in 48% HBr (1 ml) in acetic acid (5 ml). The reaction mixture was then cooled and 25 ml water was added, whereby the crude product precipitated. To the mixture was added 5 ml diethylether whereafter it was filtered to give 150 mg of the title compound, M.p. 248°-250° C.

Workup

  1. temperatureThe reaction mixture was then cooled
  2. customwhereby the crude product precipitated
  3. additionTo the mixture was added 5 ml diethylether whereafter it
  4. filtrationwas filtered

Sources & evidence

ORD record
ord-09274b26bfe84c229f8722f10e8d0ad7
Source dataset
uspto-grants-1993_04
Patent number
US05200422

Reaction notes

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