Potassium Carbonate → HCID 67015876, compound

HRID 1888722Notes

Reaction equation

HRID 1888722 reaction equation
F[C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[N+:12]([O-:14])=[O:13])[C:5]([O:7][CH3:8])=[O:6].[SH:15][CH2:16][CH2:17][C:18]([O:20][CH2:21][CH:22]([CH2:27][CH3:28])[CH2:23][CH2:24][CH2:25][CH3:26])=[O:19].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.C(OCC)(=O)C>[CH2:27]([CH:22]([CH2:23][CH2:24][CH2:25][CH3:26])[CH2:21][O:20][C:18](=[O:19])[CH2:17][CH2:16][S:15][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[N+:12]([O-:14])=[O:13])[C:5]([O:7][CH3:8])=[O:6])[CH3:28]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 926402-Ethylhexyl 3-mercaptopropionateHCID 592761Methyl 3-fluoro-4-nitrobenzoate

Product 1

HCID 67015876HCID 67015876, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Methyl 3-fluoro-4-nitrobenzoate (8.72 g, 43.8 mmol) was added to a suspension of 2-ethylhexyl 3-sulfanylpropanoate (10.5 g, 48.2 mmol) and potassium carbonate (9.08 g, 65.7 mmol) in DMF (50 mL) at room temperature, and the mixture was stirred for 16 hr. The reaction mixture was diluted with ethyl acetate, and the mixture was washed with water, 10% aqueous potassium carbonate solution and saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1 to 7:3) to give the title compound (14.4 g, yield 83%).

Workup

  1. washthe mixture was washed with water, 10% aqueous potassium carbonate solution and saturated brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. customThe solvent was evaporated under reduced pressure
  4. customthe obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1 to 7:3)

Sources & evidence

ORD record
ord-9327d4fd468c4174815911494144a67a
Source dataset
uspto-grants-2013_08
Patent number
US08501804B2

Reaction notes

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