Potassium Carbonate → 2-(3-Methyl-4-nitro-phenyl)-thioacetimidic acid 3,3,4,4,4-pentafluoro-2-oxo-butyl ester

HRID 2243278Notes

Reaction equation

HRID 2243278 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH2:11][C:12]([NH2:14])=[S:13])[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9].Br[CH2:16][C:17](=[O:25])[C:18]([F:24])([F:23])[C:19]([F:22])([F:21])[F:20].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.C(OCC)(=O)C>[F:23][C:18]([F:24])([C:19]([F:22])([F:21])[F:20])[C:17](=[O:25])[CH2:16][S:13][C:12](=[NH:14])[CH2:11][C:4]1[CH:5]=[CH:6][C:7]([N+:8]([O-:10])=[O:9])=[C:2]([CH3:1])[CH:3]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 27363551-Bromo-3,3,4,4,4-pentafluorobutan-2-oneHCID 592103882-(3-Methyl-4-nitrophenyl)ethanethioamide

Product 1

HCID 866171452-(3-Methyl-4-nitro-phenyl)-thioacetimidic acid 3,3,4,4,4-pentafluoro-2-oxo-butyl esterYield 73.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-(3-Methyl-4-nitrophenyl)-thioacetamide (1.00 g), 1-bromo-3,3,4,4,4-pentafluoro-2-butanone (1.15 g) and potassium carbonate (0.79 g) were stirred in DMF (10 ml) at room temperature for 1 hour. The reaction solution was diluted with ethyl acetate and washed with water and saturated aqueous solution of sodium chloride. After drying the organic layer with magnesium sulfate, the solvent was distilled off under the reduced pressure and the obtained residue was purified by silica gel column chromatography to obtain 2-(3-Methyl-4-nitro-phenyl)-thioacetimidic acid 3,3,4,4,4-pentafluoro-2-oxo-butyl ester (1.30 g).

Workup

  1. washwashed with water and saturated aqueous solution of sodium chloride
  2. dry with materialAfter drying the organic layer with magnesium sulfate
  3. distillationthe solvent was distilled off under the reduced pressure
  4. customthe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-e9c198d0a42f4eb79d55f7f0f2487208
Source dataset
uspto-grants-2010_03
Patent number
US07674807B2

Reaction notes

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