Acetic acid, 2-(2-chloroethyl)thio-, methyl ester → HCID 20133529, compound

HRID 845077Notes

Reaction equation

HRID 845077 reaction equation
ClC1C=C(C=CC=1)C(OO)=[O:6].[CH3:12][O:13][C:14](=[O:20])[CH2:15][S:16][CH2:17][CH2:18][Cl:19]>C(Cl)Cl>[CH3:12][O:13][C:14](=[O:20])[CH2:15][S:16]([CH2:17][CH2:18][Cl:19])=[O:6]

Participants

4

Reactant 2

HCID 51933Acetic acid, 2-(2-chloroethyl)thio-, methyl esterHCID 70297m-Chloroperbenzoic acid

Product 1

HCID 20133529HCID 20133529, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-Chloro-peroxybenzoic acid (81%, 4.7 g, 0.022 mole) was added to the title compound of Example 10 (3.7 g, 0.022 mole) in cold (5° C.) methylene chloride (75 ml) stirred for 30 minutes and cooled in a refrigerator for 48 hours. After removing the solid by filtration, a saturated solution of sodium thiosulfate (30 ml) was added and the mixture stirred for 15 minutes. The layers were separated and the organic layer was washed with saturated sodium bicarbonate (2×50 ml), dried over sodium sulfate, filtered and the solvent removed on a rotary evaporator. The residue was crystallized from ethyl acetate and hexane to give a white solid which was identified as the title compound by its NMR and IR spectra.

Workup

  1. temperaturecooled in a refrigerator for 48 hours
  2. customAfter removing the solid
  3. filtrationby filtration
  4. additiona saturated solution of sodium thiosulfate (30 ml) was added
  5. stirringthe mixture stirred for 15 minutes
  6. customThe layers were separated
  7. washthe organic layer was washed with saturated sodium bicarbonate (2×50 ml)
  8. dry with materialdried over sodium sulfate
  9. filtrationfiltered
  10. customthe solvent removed on a rotary evaporator
  11. customThe residue was crystallized from ethyl acetate and hexane
  12. customto give a white solid which

Sources & evidence

ORD record
ord-9b0e728e5ff8496ca154dbf95bfc430b
Source dataset
uspto-grants-1988_07
Patent number
US04755524

Reaction notes

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