Water → HCID 57687737, compound

HRID 2359944Notes

Reaction equation

HRID 2359944 reaction equation
[SH:1][C:2]1[NH:3][CH:4]=[C:5]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[N:6]=1.F[C:13]1[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+].[OH2:28]>CN(C)C=O>[N+:19]([C:16]1[CH:17]=[CH:18][C:13]([N:3]2[CH:4]=[C:5]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[N:6]=[C:2]2[S:1][C:13]2[CH:18]=[CH:17][C:16]([N+:19]([O-:20])=[O:28])=[CH:15][CH:14]=2)=[CH:14][CH:15]=1)([O-:21])=[O:20]

Participants

6

Reactant 4

HCID 962WaterHCID 9590p-FluoronitrobenzeneHCID 11430Potassium CarbonateHCID 178469909HCID 178469909, compound

Product 1

HCID 57687737HCID 57687737, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

Ethyl 2-mercapto-1H-imidazole-4-carboxylate (1.00 g), 1-fluoro-4-nitrobenzene (2.05 g) and anhydrous potassium carbonate (4.00 g) were mixed in N,N-dimethylformamide (30 mL), and the mixture was stirred at 100° C. for 4 hr. The reaction mixture was cooled, water was added, 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. Diisopropyl ether was added to the residue and the resulting crystals were collected by filtration to give the title compound as pale-yellow crystals (yield 2.06 g, 86%).

Workup

  1. temperatureThe reaction mixture was cooled
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. additionDiisopropyl ether was added to the residue
  7. filtrationthe resulting crystals were collected by filtration

Sources & evidence

ORD record
ord-ea67803e76904146aefcc82ccb6bbd49
Source dataset
uspto-grants-2014_04
Patent number
US08686010B2

Reaction notes

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