Sodium Thiosulfate → HCID 178445745, compound

HRID 1802073Notes

Reaction equation

HRID 1802073 reaction equation
[C:1]([C@H:5]1[CH2:10][CH2:9][C@H:8]([O:11][C:12]2[CH:13]=[C:14]3[C:19](=[CH:20][CH:21]=2)[N:18]=[CH:17][CH:16]=[CH:15]3)[CH2:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2].ClC1C=CC=C(C(OO)=[O:30])C=1.S([O-])([O-])(=O)=S.[Na+].[Na+]>CC(C)=O>[C:1]([C@H:5]1[CH2:10][CH2:9][C@H:8]([O:11][C:12]2[CH:13]=[C:14]3[C:19](=[CH:20][CH:21]=2)[N+:18]([O-:30])=[CH:17][CH:16]=[CH:15]3)[CH2:7][CH2:6]1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 178445795HCID 178445795, compound

Product 1

HCID 178445745HCID 178445745, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
23 °C

Procedure

6-(trans-4-tert-Butyl-cyclohexyloxy)-quinoline (6.11 g, 0.0216 mol) was dissolved in acetone (100 mL, Acros), followed by m-chloroperbenzoic acid (11.7 g, 0.0542 mol, Aldrich) in small portions at RT. The reaction mixture was then stirred at 23° C. for 1.5 hours. Sodium thiosulfate was added, 97.6 mL of a saturated aqueous solution. The reaction mixture was then allowed to stir for 45 minutes. Excess of solvents were removed under vacuum, and the residue was diluted with water and extracted with methylene chloride. Combined organic layers were treated with magnesium sulfate, filtered and evaporated. The residue was taken up in methylene chloride and silica gel was added. The solvents were removed. The residue was then purified via chromatography (SiO2, 0-10% MeOH/DCM) to give the product (Rf=0.19 in 5% methanol/methylene chloride). The appropriate fractions were combined to give the product in 4.99 g yield (77%).

Workup

  1. stirringto stir for 45 minutes
  2. customExcess of solvents were removed under vacuum
  3. additionthe residue was diluted with water
  4. extractionextracted with methylene chloride
  5. additionCombined organic layers were treated with magnesium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. additionsilica gel was added
  9. customThe solvents were removed
  10. customThe residue was then purified via chromatography (SiO2, 0-10% MeOH/DCM)
  11. customto give the product (Rf=0.19 in 5% methanol/methylene chloride)
  12. customto give the product in 4.99 g
  13. customyield (77%)

Sources & evidence

ORD record
ord-49f0589db3ce4b85939db4134b21b4d9
Source dataset
uspto-grants-2013_01
Patent number
US08349849B2

Reaction notes

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