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Sodium Thiosulfate → HCID 57687734, 화합물

HRID 2359957
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HRID 2359957 반응식
[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]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

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

생성물 1

HCID 57687734HCID 57687734, 화합물수율 63%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-91c91b8c152049dcb5b6acb073215268
출처 데이터셋
uspto-grants-2014_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08686010B2

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