Water → HCID 14303595, compound

HRID 845311Notes

Reaction equation

HRID 845311 reaction equation
[CH3:1][C:2]1[C:7](=[O:8])[CH:6]=[C:5]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[N:4]([C:15]2[CH:20]=[CH:19][C:18]([S:21][CH3:22])=[CH:17][CH:16]=2)[C:3]=1[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.ClC1C=CC=C(C(OO)=[O:37])C=1.O>C(Cl)Cl>[CH3:22][S:21]([C:18]1[CH:17]=[CH:16][C:15]([N:4]2[C:5]([C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=3)=[CH:6][C:7](=[O:8])[C:2]([CH3:1])=[C:3]2[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[CH:20][CH:19]=1)=[O:37]

Participants

5

Reactant 3

HCID 962WaterHCID 70297m-Chloroperbenzoic acidHCID 14303593HCID 14303593, compound

Product 1

HCID 14303595HCID 14303595, compoundYield 94.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dissolved in 30 ml of methylene chloride was 1.1 g (0.0029 mole) of 3-methyl-1-(4-methylthiophenyl)-2,6-diphenyl-4(1H)-pyridinone, followed by addition of 0.6 g (0.0034 mole) of m-chloroperbenzoic acid (as oxidizing agent). After stirring the reaction mixture for 15 minutes, it was poured into water, followed by extraction with methylene chloride. The organic layer (the extract) was washed with 20 ml of a saturated aqueous solution of sodium hydrogen carbonate and then with water. The organic layer was thereafter dried over anhydrous sodium sulfate. The solvent was distilled off and the resulting crystals were recrystallized form a 2:1 mixed solvent of acetone and hexane, affording 1.1 g of 1-(4-methanesulfinylphenyl)-3-methyl-2,6-diphenyl-4(1H)-pyridinone having a melting point of 242°-244° C.

Workup

  1. extractionfollowed by extraction with methylene chloride
  2. extractionThe organic layer (the extract)
  3. washwas washed with 20 ml of a saturated aqueous solution of sodium hydrogen carbonate
  4. dry with materialThe organic layer was thereafter dried over anhydrous sodium sulfate
  5. distillationThe solvent was distilled off
  6. customthe resulting crystals were recrystallized form a 2:1 mixed solvent of acetone and hexane

Sources & evidence

ORD record
ord-63bc30732b6a43f2a2c1d3a54698f59b
Source dataset
uspto-grants-1988_07
Patent number
US04757081

Reaction notes

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