Acetone → HCID 22364770, compound

HRID 1781629Notes

Reaction equation

HRID 1781629 reaction equation
[CH3:1][O:2][C:3](=[O:23])[C:4]1[C:5](=[CH:18][C:19]([Cl:22])=[CH:20][CH:21]=1)[NH:6][C:7](=[O:17])[CH2:8][S:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.I([O-])(=O)(=O)=[O:25].[Na+].CC(C)=O>O>[CH3:1][O:2][C:3](=[O:23])[C:4]1[C:5](=[CH:18][C:19]([Cl:22])=[CH:20][CH:21]=1)[NH:6][C:7](=[O:17])[CH2:8][S:9]([CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:25]

Participants

5

Reactant 3

HCID 180AcetoneHCID 22364772HCID 22364772, compoundHCID 23667635Sodium periodate

Product 1

HCID 22364770HCID 22364770, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2 g (5.7 mmol) of N-(benzylthio)acetyl-4-chloro-anthranilic acid methyl ester and 3.66 g (17.1 mmol) of sodium metaperiodate are dissolved in 12 ml of water and 48 ml of acetone and the resulting solution is stirred at reflux for 6 hours. The reaction mixture is allowed to cool, filtered and concentrated by evaporation. Chromatography of the crude product on silica gel with hexane/ethyl acetate yields N-(benzylsulfinyl)acetyl-4-chloro-anthranilic acid methyl ester in the form of a yellow oil interspersed with crystals.

Workup

  1. temperatureat reflux for 6 hours
  2. temperatureto cool
  3. filtrationfiltered
  4. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-50a5ddf043b5465db6af6da3b8246254
Source dataset
uspto-grants-1997_05
Patent number
US05633379

Reaction notes

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