Hydrochloric Acid → HCID 22063980, compound

HRID 1828196Notes

Reaction equation

HRID 1828196 reaction equation
[CH3:1][N:2]1[C:6]2[CH:7]=[CH:8][C:9]([CH:11]=[C:12]([N+]([O-])=O)[CH3:13])=[CH:10][C:5]=2[N:4]([CH3:17])[C:3]1=[O:18].O.Cl.C(=O)(O)[O-:22].[Na+]>CO.[Fe].O.O.O.O.O.O.[Fe](Cl)(Cl)Cl>[CH3:1][N:2]1[C:6]2[CH:7]=[CH:8][C:9]([CH2:11][C:12](=[O:22])[CH3:13])=[CH:10][C:5]=2[N:4]([CH3:17])[C:3]1=[O:18]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 516892Sodium BicarbonateHCID 69585481HCID 69585481, compound

Product 1

HCID 22063980HCID 22063980, compound

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 16211236Trichloroiron;hexahydrateCatalystHCID 887MethanolSolvent

Conditions

Temperature
75 °C

Procedure

1,3-Dimethyl-5-(2-nitro-propenyl)-1,3-dihydro-benzoimidazol-2-one (2.23 g) was dissolved in methanol (15 mL) and water (40 mL) and treated sequentially with iron (1.67 g) and iron trichloride hexahydrate (174.3 mg). After heating to 75° C. concentrated hydrochloric acid (8 mL) was added in portions over 0.5 hours. The mixture was stirred at 75° C. for 2.5 hours, cooled, treated with saturated sodium bicarbonate and extracted into ethyl acetate The organic layer was dried over sodium sulfate, and concentrated to give 1,3-Dimethyl-5-(2-oxo-propyl)-1,3-dihydro-benzoimidazol-2-one (1.465 g).

Workup

  1. additionwas added in portions over 0.5 hours
  2. temperaturecooled
  3. extractionextracted into ethyl acetate The organic layer
  4. dry with materialwas dried over sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-59a49a151db24a059dec891f9c55a883
Source dataset
uspto-grants-2006_06
Patent number
US07056918B2

Reaction notes

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