Water → HCID 69983297, compound

HRID 2231118Notes

Reaction equation

HRID 2231118 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([C:26]3[S:27][CH:28]=[CH:29][CH:30]=3)=[C:10]([C:14]([C:16]([C:18]3[CH:23]=[CH:22][C:21]([CH3:24])=[C:20]([F:25])[CH:19]=3)=[O:17])=[O:15])[CH:11]=[CH:12][CH:13]=2)=[CH:4][CH:3]=1.[CH3:31][S:32]([O-:34])=[O:33].[Na+].O>CN(C)C=O>[CH3:31][S:32]([C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([C:26]3[S:27][CH:28]=[CH:29][CH:30]=3)=[C:10]([C:14]([C:16]([C:18]3[CH:23]=[CH:22][C:21]([CH3:24])=[C:20]([F:25])[CH:19]=3)=[O:17])=[O:15])[CH:11]=[CH:12][CH:13]=2)=[CH:4][CH:3]=1)(=[O:34])=[O:33]

Participants

5

Reactant 3

HCID 962WaterHCID 2733271Sodium methanesulfinateHCID 69984861HCID 69984861, compound

Product 1

HCID 69983297HCID 69983297, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of the benzil from Step 3 (2 g, 6.8 mmol) and sodium methylsulfinate (775 mg, 7.1 mmol) in dimethylformamide (10 ml) was stirred at 90° C. for 16 hours. The reaction was cooled, poured into water (120 ml) and the mixture was extracted with methylene chloride. The organic layer was dried over sodium sulfate, filtered and the filtrate concentrated. The residue was recrystallized from ethyl acetate and hexane to give 760 mg (45%) of the desired sulfone: mp 130-132° C. Anal. Calc'd. for C16H13FO4S2 (MW 352.41): C, 54.53; H, 3.72; S, 18.20. Found: C, 54.20; H, 3.51; S, 18.40.

Workup

  1. temperatureThe reaction was cooled
  2. extractionthe mixture was extracted with methylene chloride
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationthe filtrate concentrated
  6. customThe residue was recrystallized from ethyl acetate and hexane

Sources & evidence

ORD record
ord-b17a2ba5b5454591b2e6cbe05555e10f
Source dataset
uspto-grants-2002_07
Patent number
US06426360B1

Reaction notes

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