3-Hydroperoxyphthalic acid → HCID 178504627, compound

HRID 466068Notes

Reaction equation

HRID 466068 reaction equation
[CH3:1][C:2]([C:5]1[CH:10]=[C:9]([C:11]2[NH:12][N:13]=[C:14]([S:16][CH3:17])[N:15]=2)[CH:8]=[C:7]([C:18]([CH3:21])([CH3:20])[CH3:19])[C:6]=1[OH:22])([CH3:4])[CH3:3].C1C=C([O:29]O)C(C(O)=O)=C(C(O)=O)C=1>C(O)C.O>[CH3:19][C:18]([C:7]1[CH:8]=[C:9]([C:11]2[NH:12][N:13]=[C:14]([S:16]([CH3:17])=[O:29])[N:15]=2)[CH:10]=[C:5]([C:2]([CH3:1])([CH3:3])[CH3:4])[C:6]=1[OH:22])([CH3:21])[CH3:20]

Participants

5

Reactant 2

HCID 198097063-Hydroperoxyphthalic acidHCID 135786541HCID 135786541, compound

Product 1

HCID 178504627HCID 178504627, compoundYield 30%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A 50° C. solution of 1.0 g (3.13 mmol) of the methylthiotriazole (Example 43) in 50 ml of 95% ethanol is treated dropwise with a solution of 0.92 g (2.98 mmol) of 80% monoperoxyphthalic acid, magnesium salt (MMPP) in 4.5 ml of water over 20 minutes. The resulting reaction mixture is stirred at 40° to 50° C. for two hours and concentrated in vacuo. The residue is dissolved in ethyl acetate, extracted with saturated aqueous NaHCO3 (three times), water and brine, dried over Na2SO4 and concentrated in vacuo. Flash chromatography (SiO2, 5% methanol-chloroform, 26×6.5 cm) followed by recrystallization from acetone-water gives 0.30 g (1.05 g theor., 29%) of the sulfoxide as a white solid, mp 135°-145° C.

Workup

  1. customThe resulting reaction mixture
  2. concentrationconcentrated in vacuo
  3. dissolutionThe residue is dissolved in ethyl acetate
  4. extractionextracted with saturated aqueous NaHCO3 (three times), water and brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. customFlash chromatography (SiO2, 5% methanol-chloroform, 26×6.5 cm) followed by recrystallization from acetone-water

Sources & evidence

ORD record
ord-c04c8efc2f6440ada82dbd7c72151bf7
Source dataset
uspto-grants-1992_10
Patent number
US05155122

Reaction notes

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