Dimethylformamide → HCID 877679, compound

HRID 856782Notes

Reaction equation

HRID 856782 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1.[SH:11][C:12]1[N:13]([CH3:17])[CH:14]=[CH:15][N:16]=1.C(=O)([O-])[O-].[K+].[K+].CN(C=O)C>O>[CH3:17][N:13]1[CH:14]=[CH:15][N:16]=[C:12]1[S:11][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 9590p-FluoronitrobenzeneHCID 11430Potassium CarbonateHCID 178480602HCID 178480602, compound

Product 1

HCID 877679HCID 877679, compoundYield 87.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1-fluoro-4-nitrobenzene (5.0 g), 2-mercapto-1-methylimidazole (4.04 g) and potassium carbonate (14.7 g) were added to. DMF (100 ml), and the mixture was stirred for 2 hours under argon atmosphere at 130° C. After the mixture was allowed to be at room temperature, water was added to the mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with water three times, further washed with saturated brine, and dried over magnesium sulfate. The solvent was distilled off under reduced pressure, and the obtained residue was recrystallized from ethyl acetate-diisopropyl ether, to give 1-methyl-2-[(4-nitrophenyl)thio]imidazole (7.29 g) as yellow crystals.

Workup

  1. customto be at room temperature
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with water three times
  4. washfurther washed with saturated brine
  5. dry with materialdried over magnesium sulfate
  6. distillationThe solvent was distilled off under reduced pressure
  7. customthe obtained residue was recrystallized from ethyl acetate-diisopropyl ether

Sources & evidence

ORD record
ord-e1f5f21a5acb4ffca2759b835b2067b2
Source dataset
uspto-grants-2007_08
Patent number
US07262185B2

Reaction notes

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