Diphosgene → 2,3-dihydro-2-oxo-1H-benzimidazol-1-ylcarbonyl chloride

HRID 1588499Notes

Reaction equation

HRID 1588499 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[NH:3][C:2]1=[O:10].[Cl:11][C:12]([O:15]C(Cl)=O)(Cl)Cl>O1CCCC1>[O:10]=[C:2]1[N:3]([C:12]([Cl:11])=[O:15])[C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=2[NH:1]1

Participants

4

Reactant 2

HCID 10426DiphosgeneHCID 119852-Hydroxy benzimidazole

Product 1

HCID 105840642,3-dihydro-2-oxo-1H-benzimidazol-1-ylcarbonyl chloride

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

It was prepared by suspending 5 g of 2,3-dihydro-1H-benzimidazole-2-one in 200 ml of distilled tetrahydrofuran and by adding 13.5 ml of trichloromethylchloroformate. The reaction mixture was refluxed for 3 hrs until a clear solution was obtained. After cooling the separated solid was removed by filtration and after concentration to dryness of the mother liquors 6.5 g of the title compound were obtained.

Workup

  1. customIt was prepared
  2. temperatureThe reaction mixture was refluxed for 3 hrs until a clear solution
  3. customwas obtained
  4. temperatureAfter cooling the separated solid
  5. customwas removed by filtration
  6. concentrationafter concentration to dryness of the mother liquors 6.5 g of the title compound
  7. customwere obtained

Sources & evidence

ORD record
ord-83b7ba3b53eb4122bbaeb38c59ed7aae
Source dataset
uspto-grants-1993_06
Patent number
US05223511

Reaction notes

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