Ethyl Acetate → Acetate

HRID 1781622Notes

Reaction equation

HRID 1781622 reaction equation
[CH:1]1[CH:6]=[CH:5][C:4]([CH2:7][CH2:8][CH2:9][SH:10])=[CH:3][CH:2]=1.[H-].[Na+].[CH3:13][O:14][C:15](=[O:28])[C:16]1[C:17](=[CH:23][C:24]([Cl:27])=[CH:25][CH:26]=1)[NH:18][C:19](=[O:22])[CH2:20]Br.C(OCC)(=O)C>O1CCCC1>[C:15]([O-:28])(=[O:14])[CH3:16].[CH3:13][O:14][C:15](=[O:28])[C:16]1[C:17](=[CH:23][C:24]([Cl:27])=[CH:25][CH:26]=1)[NH:18][C:19](=[O:22])[CH2:20][S:10][CH2:9][CH2:8][CH2:7][C:4]1[CH:5]=[CH:6][CH:1]=[CH:2][CH:3]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 905963-Phenylpropane-1-thiolHCID 22364781HCID 22364781, compound

Product 2

HCID 175AcetateHCID 22364792HCID 22364792, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

4.3 g (28.7 mmol) of 3-phenylpropylthiol are added dropwise at 0° to a mixture of 1.4 g (31.6 mmol) of sodium hydride dispersion in oil (55%) and 30 ml of tetrahydrofuran. The mixture is then stirred for 30 minutes at 0°. A solution of 4-chloro-N-(bromoacetyl)-anthranilic acid methyl ester in 30 ml of tetrahydrofuran is added dropwise and the mixture is then stirred for one hour at 0° and for three hours at room temperature. Ethyl acetate is added and the reaction mixture is extracted with water and brine. The aqueous phases are washed with ethyl acetate and the organic phases are combined, dried over sodium sulfate, filtered and concentrated by evaporation. Chromatography on silica gel with hexanelethyl acetate (4:1) yields 4-chloro-N-(3-phenylpropylthio)acetylanthranilic acid methyl ester in the form of a yellow oil.

Workup

  1. stirringthe mixture is then stirred for one hour at 0° and for three hours at room temperature
  2. extractionthe reaction mixture is extracted with water and brine
  3. washThe aqueous phases are washed with ethyl acetate
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-b65637eaee214615974c0cc5a630c36a
Source dataset
uspto-grants-1997_05
Patent number
US05633379

Reaction notes

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