ethanone, 2-[(4-chlorophenyl)thio]-1-phenyl- → HCID 13319308, compound
Reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH2:9][C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:11])=[CH:4][CH:3]=1.I([O-])(=O)(=O)=[O:19].[Na+]>COCCOC>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([CH2:9][C:10]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)=[O:11])=[O:19])=[CH:6][CH:7]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 40 °C
Procedure
To a vigorously stirred solution of 199 g. (0.75 mole) of 4-chloro-2-(phenylthio)acetophenone in 2 liters of 1,2-dimethoxyethane (glyme) is added a solution of 175.5 g. (0.825 mole) of sodium periodate; the mixture is heated at 40°C for 7 days. The mixture is then filtered from the inorganic materials and the glyme distilled from the filtrate to give a slurry of crystals. These are filtered and this mixture of sulfoxide and starting material is separated from the inorganic contaminants by extraction into abs. ethanol. After filtration and concentration, the residue is dissolved in 1.5 liters of boiling hexane to give (after cooling and filtration) 91.8 g. of product, melting point 129°-130°C.
Workup
- filtrationThe mixture is then filtered from the inorganic materials
- distillationthe glyme distilled from the filtrate
- customto give a slurry of crystals
- filtrationThese are filtered
- additionthis mixture of sulfoxide
- customis separated from the inorganic contaminants by extraction into abs
- filtrationAfter filtration and concentration
- dissolutionthe residue is dissolved in 1.5 liters of boiling hexane
- customto give
- temperature(after cooling and filtration) 91.8 g
Sources & evidence
- ORD record
- ord-c7ab1cc9d8d147eea7141917a874821d
- Source dataset
- uspto-grants-1976_05
- Patent number
- US03957769
Reaction notes
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