Sodium Thiosulfate → HCID 57687734, compound

HRID 2359957Notes

Reaction equation

HRID 2359957 reaction equation
[CH3:1][N:2]([CH2:10][C:11]1[S:12][C:13](SC2C=CC=CC=2)=[C:14]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[N:15]=1)[C:3](=[O:9])[O:4][C:5]([CH3:8])([CH3:7])[CH3:6].Cl[C:30]1[CH:35]=[CH:34][CH:33]=[C:32](C(OO)=O)[CH:31]=1.[S:40]([O-:44])([O-])(=[O:42])=S.[Na+].[Na+]>CN(C)C=O>[CH3:1][N:2]([CH2:10][C:11]1[S:12][C:13]([S:40]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)(=[O:44])=[O:42])=[C:14]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[N:15]=1)[C:3](=[O:9])[O:4][C:5]([CH3:8])([CH3:6])[CH3:7]

Participants

5

Reactant 3

HCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 57687741HCID 57687741, compound

Product 1

HCID 57687734HCID 57687734, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of tert-butyl methyl{[4-phenyl-5-(phenylthio)-1,3-thiazol-2-yl]methyl}carbamate (0.27 g) in N,N-dimethylformamide (3 mL) was added 3-chloroperbenzoic acid (0.57 g) under ice-cooling, and the mixture was stirred at room temperature for 30 min. Aqueous sodium thiosulfate solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated aqueous sodium hydrogen carbonate solution, water and saturated brine in this order, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was dissolved in acetic acid (2 mL), 3-chloroperbenzoic acid (0.96 g) was added thereto, and the mixture was stirred at room temperature for 30 min. Aqueous sodium thiosulfate solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated aqueous sodium hydrogen carbonate solution, water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent:hexane-ethyl acetate=2:1) to give the title compound as a pale-yellow oil (yield 0.18 g, 63%).

Workup

  1. temperaturecooling
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with saturated aqueous sodium hydrogen carbonate solution, water and saturated brine in this order
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. dissolutionThe residue was dissolved in acetic acid (2 mL)
  7. addition3-chloroperbenzoic acid (0.96 g) was added
  8. stirringthe mixture was stirred at room temperature for 30 min
  9. additionAqueous sodium thiosulfate solution was added to the reaction mixture
  10. extractionthe mixture was extracted with ethyl acetate
  11. washThe extract was washed with saturated aqueous sodium hydrogen carbonate solution, water and saturated brine
  12. dry with materialdried over anhydrous magnesium sulfate
  13. concentrationconcentrated under reduced pressure
  14. customThe residue was purified by silica gel column chromatography (eluent:hexane-ethyl acetate=2:1)

Sources & evidence

ORD record
ord-91c91b8c152049dcb5b6acb073215268
Source dataset
uspto-grants-2014_04
Patent number
US08686010B2

Reaction notes

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