Iodine chloride → HCID 22287489, compound

HRID 2301069Notes

Reaction equation

HRID 2301069 reaction equation
[I:1]Cl.[N:3]1[C:4](=[O:12])[N:5]=[C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=12>C(O)(=O)C>[I:1][C:10]1[CH:9]=[CH:8][C:7]2=[N:3][C:4](=[O:12])[N:5]=[C:6]2[CH:11]=1

Participants

4

Reactant 2

HCID 24640Iodine chlorideHCID 162542Benzimidazol-2-one

Product 1

HCID 22287489HCID 22287489, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of iodine monochloride and 2H-benzimidazole-2-one (0.67 g) (Method 59) in glacial acetic acid (8 ml) was heated to 80° C. for 1 hour then cooled. The mixture was partitioned between saturated aqueous sodium sulphite solution and DCM. The organic layer was evaporated to dryness then redissolved in ethyl acetate. The aqueous layer was extracted with ethyl acetate then all ethyl acetate extracts were combined and washed with saturated aqueous sodium hydrogencarbonate solution, water and brine. The organic extracts were passed through a Varian Chem Elut column and washed through with ethyl acetate. Volatile material was removed by evaporation to give the title compound (0.36 g) as a solid which was used without further purification. MS (ESP−): 261 (M+H)+.

Workup

  1. temperaturethen cooled
  2. customThe mixture was partitioned between saturated aqueous sodium sulphite solution and DCM
  3. customThe organic layer was evaporated to dryness
  4. dissolutionthen redissolved in ethyl acetate
  5. extractionThe aqueous layer was extracted with ethyl acetate
  6. washwashed with saturated aqueous sodium hydrogencarbonate solution, water and brine
  7. washwashed through with ethyl acetate
  8. customVolatile material was removed by evaporation

Sources & evidence

ORD record
ord-50700de48396435e970fee060dc14725
Source dataset
uspto-grants-2002_12
Patent number
US06498275B1

Reaction notes

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