HCID 14064788, compound → HCID 20222292, compound

HRID 980157Notes

Reaction equation

HRID 980157 reaction equation
I([O-])(=O)(=O)=[O:2].[Na+].[C:7]([C:9]1[CH:27]=[CH:26][C:12]([NH:13][C:14](=[O:25])[C:15]([OH:24])([C:20]([F:23])([F:22])[F:21])[CH2:16][S:17][CH2:18][CH3:19])=[CH:11][C:10]=1[C:28]([F:31])([F:30])[F:29])#[N:8]>O.CO>[C:7]([C:9]1[CH:27]=[CH:26][C:12]([NH:13][C:14](=[O:25])[C:15]([OH:24])([C:20]([F:21])([F:22])[F:23])[CH2:16][S:17]([CH2:18][CH3:19])=[O:2])=[CH:11][C:10]=1[C:28]([F:30])([F:31])[F:29])#[N:8]

Participants

5

Reactant 2

HCID 14064788HCID 14064788, compoundHCID 23667635Sodium periodate

Product 1

HCID 20222292HCID 20222292, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of sodium metaperiodate (0.407 g.) in water (15 ml.) was added dropwise to a stirred solution of 4-cyano-3-trifluoromethyl-N-(3-ethylthio-2-hydroxy-2-trifluoromethylpropionyl)aniline (0.6 g.) in methanol (25 ml.) and the mixture was stirred at laboratory temperature for 48 hours and then filtered. The solid was washed with methanol (25 ml.) and the mixture was filtered, and the combined filtrates were evaporated to dryness under reduced pressure. The residue was dissolved in ethyl acetate (150 ml.) and the solution was washed successively with water (15 ml.), saturated aqueous sodium sulphite solution (25 ml.) and saturated aqueous sodium chloride solution (25 ml.), dried over magnesium sulphate and evaporated to dryness under reduced pressure. The residue was chromatographed on silica gel (Merck 7734) using a 1:1 v/v mixture of ethyl acetate and petroleum ether (b.p. 60°-80° C.) as eluant, and the two diastereoisomers of 4-cyano-3-trifluoromethyl-N-(3-ethylsulphinyl-2-hydroxy-2-trifluoromethylpropionyl)aniline were obtained by evaporation of the appropriate fractions of the eluate. These had m.p. 141°-143° C. (more polar isomer) and 160°-162° C. (less polar isomer).

Workup

  1. filtrationfiltered
  2. washThe solid was washed with methanol (25 ml.)
  3. filtrationthe mixture was filtered
  4. customthe combined filtrates were evaporated to dryness under reduced pressure
  5. dissolutionThe residue was dissolved in ethyl acetate (150 ml.)
  6. washthe solution was washed successively with water (15 ml.), saturated aqueous sodium sulphite solution (25 ml.) and saturated aqueous sodium chloride solution (25 ml.)
  7. dry with materialdried over magnesium sulphate
  8. customevaporated to dryness under reduced pressure
  9. customThe residue was chromatographed on silica gel (Merck 7734)
  10. additiona 1:1 v/v mixture of ethyl acetate and petroleum ether (b.p. 60°-80° C.) as eluant

Sources & evidence

ORD record
ord-5a949247749c476c9f40b7deb2a95806
Source dataset
uspto-grants-1987_01
Patent number
US04636505

Reaction notes

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