Water → HCID 21266791, compound

HRID 566605Notes

Reaction equation

HRID 566605 reaction equation
[Cl:1][C:2]1[N:6]([CH:7]([F:9])[F:8])[C:5]([CH3:10])=[N:4][C:3]=1[C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[C:13]([N+:18]([O-])=O)[CH:12]=1.O.C(OCC)(=O)C>CO.C(O)(=O)C.[Fe]>[Cl:17][C:14]1[CH:15]=[CH:16][C:11]([C:3]2[N:4]=[C:5]([CH3:10])[N:6]([CH:7]([F:9])[F:8])[C:2]=2[Cl:1])=[CH:12][C:13]=1[NH2:18]

Participants

7

Reactant 3

HCID 962WaterHCID 8857Ethyl AcetateHCID 21266798HCID 21266798, compound

Product 1

HCID 21266791HCID 21266791, compound

Reagents, catalysts & solvents 3

HCID 23925IronCatalyst2×HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

7 g (22 mmol) of 5-chloro-4-(4-chloro-3-nitrophenyl)-1-difluoromethyl-2-methyl-1H-imidazole were dissolved in 200 ml of methanol with heating. This solution was added dropwise to a suspension of 3.6 g (65 mmol) of iron powder in 150 ml of glacial acetic acid, stirred at reflux temperature. After 3 hours, the reaction mixture was poured into 500 ml of water. A further 500 ml of ethyl acetate were added to the mixture, whereupon the iron residues were filtered off. The aqueous phase was separated off and mixed with another 500 ml of ethyl acetate. The combined organic phases were washed with water and saturated aqueous sodium chloride solution, dried over magnesium sulfate and finally concentrated. To remove the remaining acetic acid, the crude product was treated with 100 ml of toluene, whereupon the mixture was again concentrated to dryness. Yield: 5.7 g.

Workup

  1. temperaturewith heating
  2. temperatureat reflux temperature
  3. filtrationwere filtered off
  4. customThe aqueous phase was separated off
  5. additionmixed with another 500 ml of ethyl acetate
  6. washThe combined organic phases were washed with water and saturated aqueous sodium chloride solution
  7. dry with materialdried over magnesium sulfate
  8. concentrationfinally concentrated
  9. customTo remove the remaining acetic acid
  10. additionthe crude product was treated with 100 ml of toluene, whereupon the mixture
  11. concentrationwas again concentrated to dryness

Sources & evidence

ORD record
ord-f50cf60490f24744b82c49c6b111752a
Source dataset
uspto-grants-2001_01
Patent number
US06175007B1

Reaction notes

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