Methyl iodide → HCID 5303056, compound

HRID 2401489Notes

Reaction equation

HRID 2401489 reaction equation
[Cl:1][C:2]1[C:11]([N+:12]([O-:14])=[O:13])=[CH:10][C:5]2[NH:6][C:7](=O)[NH:8][C:4]=2[CH:3]=1.[C:15](=[O:18])([O-])[O-].[K+].[K+].I[CH3:22]>CN(C=O)C>[Cl:1][C:2]1[C:11]([N+:12]([O-:14])=[O:13])=[CH:10][C:5]2[N:6]([CH3:22])[C:15](=[O:18])[N:8]([CH3:7])[C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 145662265-Chloro-1,3-dihydro-6-nitro-2H-benzimidazol-2-one

Product 1

HCID 5303056HCID 5303056, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
75 °C

Procedure

5-Chloro-6-nitro-1H-benzo[d]imidazol-2(3H)-one (1.00 g, 4.7 mmol) was stirred in DMF (50 mL) then potassium carbonate (1.29 g, 9.4 mmol) and iodomethane (2.66 g, 18.7 mmol) were added. The reaction was stirred at 75° C. for 1.5 h. The reaction was allowed to cool and solvents were removed under reduced pressure. The residue was partitioned between water and ethyl acetate and the phases were separated. The aqueous phase was extracted with ethyl acetate and the combined organic extracts were through a phase separation cartridge and evaporated to afford a brown solid (1.07 g, 95%), which was taken through to the next step with no further purification.

Workup

  1. temperatureto cool
  2. customsolvents were removed under reduced pressure
  3. customThe residue was partitioned between water and ethyl acetate
  4. customthe phases were separated
  5. extractionThe aqueous phase was extracted with ethyl acetate
  6. customthe combined organic extracts were through a phase separation cartridge
  7. customevaporated

Sources & evidence

ORD record
ord-5c6a789b5b924062a002ea32e538ff52
Source dataset
uspto-grants-2014_08
Patent number
US08796296B2

Reaction notes

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