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

HRID 2222523Notes

Reaction equation

HRID 2222523 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-2d747a65f2804dff97023f149b65e368
Source dataset
uspto-grants-2008_05
Patent number
US07371743B2

Reaction notes

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