Sodium Thiosulfate → HCID 15645294, compound

HRID 1666779Notes

Reaction equation

HRID 1666779 reaction equation
C1(S[C:8]2[CH:9]=[C:10]([CH:14]3[O:18][CH2:17][CH2:16][O:15]3)[CH:11]=[CH:12][CH:13]=2)C=CC=CC=1.Cl[C:20]1[CH:25]=[CH:24][CH:23]=[C:22](C(OO)=O)[CH:21]=1.[S:30]([O-:34])([O-])(=[O:32])=S.[Na+].[Na+].C(=O)(O)[O-].[Na+]>ClCCl>[C:20]1([S:30]([C:12]2[CH:11]=[C:10]([CH:14]3[O:15][CH2:16][CH2:17][O:18]3)[CH:9]=[CH:8][CH:13]=2)(=[O:34])=[O:32])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

6

Reactant 4

HCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 19421799HCID 19421799, compound

Product 1

HCID 15645294HCID 15645294, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-78 °C

Procedure

Combine 2-(3-phenylsulfanylphenyl)-[1,3]-dioxolane (1.0 g, 3.6 mmol) and dichloromethane (15 ml). Cool to about −78° C. Add a slurry of m-chloroperbenzoic acid (2.3 g, 7.2 mmol) in dichloromethane (10 ml). After 30 minutes, warm to room temperature then add a solution 1N of sodium thiosulfate (20 ml). After 15 minutes, add a solution of saturated sodium bicarbonate. Separate the organic layer and extract the aqueous layer with dichloromethane, combine the organic layers and wash sequentially with distilled water and brine and then dry (Na2SO4), filter, and concentrate to give a residue. Chromatograph the residue eluting with EtOAc to give the title compound.

Workup

  1. temperaturewarm to room temperature
  2. waitAfter 15 minutes
  3. customSeparate the organic layer
  4. extractionextract the aqueous layer with dichloromethane
  5. washwash sequentially with distilled water and brine
  6. dry with materialdry (Na2SO4)
  7. filtrationfilter
  8. concentrationconcentrate
  9. customto give a residue
  10. washChromatograph the residue eluting with EtOAc

Sources & evidence

ORD record
ord-01fb8923aad14bac9abaed58127052fb
Source dataset
uspto-grants-2011_10
Patent number
US08044090B2

Reaction notes

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