Sodium Thiosulfate → HCID 178527306, compound

HRID 585720Notes

Reaction equation

HRID 585720 reaction equation
C1(S[C@H:8]2[CH2:13][CH2:12][C@H:11]([C:14]3[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][C:15]=3[OH:21])[CH2:10][CH2:9]2)C=CC=CC=1.Cl[C:23]1[CH:28]=[CH:27][CH:26]=[C:25](C(OO)=O)[CH:24]=1.[S:33]([O-:37])([O-])(=[O:35])=S.[Na+].[Na+]>ClCCl>[C:23]1([S:33]([C@H:8]2[CH2:13][CH2:12][C@H:11]([C:14]3[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][C:15]=3[OH:21])[CH2:10][CH2:9]2)(=[O:37])=[O:35])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 178516060HCID 178516060, compound

Product 1

HCID 178527306HCID 178527306, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A round bottom flask containing trans-4-[4-(phenylsulfanyl)cyclohexyl]-1,3-benzenediol (18 mg, 0.06 mmol) and dichloromethane (2 ml) was cooled to 0° C. and meta-chloroperbenzoic acid (50-60%, 41 mg, 0.24 mmol) was added with stirring. After 30 min at this temperature the reaction mixture was poured into saturated sodium thiosulfate solution (5 ml) and partitioned between saturated aqueous sodium hydrogen carbonate (10 ml) and dichloromethane (10 ml). The aqueous phase was further extracted with dichloromethane (2×10 ml) and the combined organic extracts were washed with brine, dried over magnesium sulfate and concentrated in vacuo. Purification via flash column chromatography (SiO2, ethyl acetate/petrol, 30:70) afforded the title compound (6 mg, 30%) as an off-white solid. δH (d4-MeOH) 1.40-1.62 (4H, m), 1.88-1.95 (2H, m), 2.05-2.13 (2H, m), 2.72 (1H, m), 3.18 (1H, m), 6.08-6.13 (2H, m), 6.82 (1H, d), 7.64 (2H, m), 7.75 (1H, m), 7.90 (2H, m); m/z (ES+) 333 (M+H)+.

Workup

  1. custompartitioned between saturated aqueous sodium hydrogen carbonate (10 ml) and dichloromethane (10 ml)
  2. extractionThe aqueous phase was further extracted with dichloromethane (2×10 ml)
  3. washthe combined organic extracts were washed with brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customPurification via flash column chromatography (SiO2, ethyl acetate/petrol, 30:70)

Sources & evidence

ORD record
ord-821536b148b046888a2255bafe1eda7f
Source dataset
uspto-grants-2005_08
Patent number
US06933319B2

Reaction notes

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