Water → HCID 57687717, compound

HRID 1670872Notes

Reaction equation

HRID 1670872 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH:14]=[C:13]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[N:12]=[C:11]2[S:20][C:21]2[CH:26]=[CH:25][C:24]([N+:27]([O-])=O)=[CH:23][CH:22]=2)=[CH:6][CH:5]=1)([O-])=O.[Cl-].[Ca+2].[Cl-].O>C(O)C.[Fe]>[NH2:1][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH:14]=[C:13]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[N:12]=[C:11]2[S:20][C:21]2[CH:22]=[CH:23][C:24]([NH2:27])=[CH:25][CH:26]=2)=[CH:6][CH:5]=1

Participants

6

Reactant 3

HCID 962WaterHCID 5284359Calcium ChlorideHCID 57687737HCID 57687737, compound

Product 1

HCID 57687717HCID 57687717, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Procedure

Ethyl 1-(4-nitrophenyl)-2-[(4-nitrophenyl)thio]-1H-imidazole-4-carboxylate (3.00 g) was suspended in ethanol (120 mL), iron powder (4.05 g), anhydrous calcium chloride (0.81 g) and water (20 mL) were added, and the mixture was heated under reflux for 4 hr. The reaction mixture was allowed to cool, and filtered. Saturated aqueous sodium hydrogen carbonate solution was added to the obtained filtrate, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. Methanol (30 mL) was added to the residue and the resulting crystals were collected by filtration to give the title compound as pale-yellow crystals (yield 2.00 g, 78%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 4 hr
  3. temperatureto cool
  4. filtrationfiltered
  5. additionSaturated aqueous sodium hydrogen carbonate solution was added to the obtained filtrate
  6. extractionthe mixture was extracted with ethyl acetate
  7. washThe extract was washed with saturated brine
  8. dry with materialdried over anhydrous magnesium sulfate
  9. concentrationconcentrated under reduced pressure
  10. additionMethanol (30 mL) was added to the residue
  11. filtrationthe resulting crystals were collected by filtration

Sources & evidence

ORD record
ord-21c929399f2c487d902ca44e6c4d1350
Source dataset
uspto-grants-2011_08
Patent number
US07994205B2

Reaction notes

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