Sodium Hydroxide → 3-Chloro-4-(1,1-dioxo-[1,2]thiazinan-2-yl)-benzoic acid

HRID 1629869Notes

Reaction equation

HRID 1629869 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH3:16])[CH:5]=[CH:6][C:7]=1[N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][S:9]1(=[O:15])=[O:14].[Mn]([O-])(=O)(=O)=[O:18].[K+].[OH-:23].[Na+].S([O-])([O-])(=O)=S.[Na+].[Na+]>O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][C:7]=1[N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][S:9]1(=[O:15])=[O:14])[C:16]([OH:18])=[O:23]

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 24477Sodium ThiosulfateHCID 516875Potassium PermanganateHCID 667317213-Chloro-4-(1,1-dioxo-[1,2]thiazinan-2-yl)-toluene

Product 1

HCID 673672553-Chloro-4-(1,1-dioxo-[1,2]thiazinan-2-yl)-benzoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

250 mg (0.96 mmol) 3-chloro-4-(1,1-dioxo-[1,2]thiazinan-2-yl)-toluene are suspended in 10 ml of water and combined with 456 mg (2.89 mmol) potassium permanganate and 39 mg (0.98 mmol) sodium hydroxide. The reaction mixture is refluxed for 4 hours. After cooling to ambient temperature sodium thiosulphate is added to decolorise the mixture which is then extracted with ethyl acetate. The combined organic phases are dried over sodium sulphate and evaporated down i. vac. The residue is purified by chromatography on silica gel (eluant: dichloromethane/methanol=19:1).

Workup

  1. temperatureThe reaction mixture is refluxed for 4 hours
  2. additionis added to decolorise the mixture which
  3. extractionis then extracted with ethyl acetate
  4. dry with materialThe combined organic phases are dried over sodium sulphate
  5. customevaporated down i
  6. customThe residue is purified by chromatography on silica gel (eluant: dichloromethane/methanol=19:1)

Sources & evidence

ORD record
ord-83b5b74e819d44c38718dd3b9e74dea3
Source dataset
uspto-grants-2014_07
Patent number
US08791103B2

Reaction notes

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