HCID 13690975, compound → HCID 13690976, compound

HRID 2290778Notes

Reaction equation

HRID 2290778 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:15]=[CH:16][C:17]=1[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH:5]([C:7]1[O:11][N:10]=[C:9]([CH2:12][S:13][CH3:14])[N:8]=1)[CH3:6].I([O-])(=O)(=O)=[O:25].[Na+]>C(O)C.O>[F:1][C:2]1[CH:3]=[C:4]([CH:15]=[CH:16][C:17]=1[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH:5]([C:7]1[O:11][N:10]=[C:9]([CH2:12][S:13]([CH3:14])=[O:25])[N:8]=1)[CH3:6]

Participants

5

Reactant 2

HCID 13690975HCID 13690975, compoundHCID 23667635Sodium periodate

Product 1

HCID 13690976HCID 13690976, compoundYield 100.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

To a solution of 0.95 g of 5-(3-fluoro-4-phenyl-α-methylbenzyl)-3-methylthiomethyl-1,2,4-oxadiazole in 150 ml of ethanol was added a solution of 1.36 g of sodium metaperiodate in 50 ml of water. After stirring with reflux for 9 hours, the reaction mixture was cooled, diluted with water and extracted with chloroform. The extracts were washed with water, dried over sodium sulfate and evaporated under reduced pressure. The residue was chromatographed over silica gel using chloroform to yield 1.0 g of 5-(3-fluoro-4-phenyl-α-methylbenzyl)-3-methylsulfinylmethyl- 1,2,4-oxadiazole. It was recrystallized from ethyl acetate-diisopropyl ether to give colorless needles, m.p. 71°-72° C. (decomp.).

Workup

  1. temperaturewith reflux for 9 hours
  2. temperaturethe reaction mixture was cooled
  3. extractionextracted with chloroform
  4. washThe extracts were washed with water
  5. dry with materialdried over sodium sulfate
  6. customevaporated under reduced pressure
  7. customThe residue was chromatographed over silica gel

Sources & evidence

ORD record
ord-b08252d25628460b88e0ab8be8d3c6dc
Source dataset
uspto-grants-1986_10
Patent number
US04618617

Reaction notes

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