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Sodium Thiosulfate → (3-Nitro-5-chloro-pyridin-2-yl)-(2,4-dimethyl-pyridin-3-yl)-methanone

HRID 1898105
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Reaktionsgleichung

Reaktionsgleichung von HRID 1898105
[Cl:1][C:2]1[CH:3]=[C:4]([N+:18]([O-:20])=[O:19])[C:5]([CH:8]([C:10]2[C:11]([CH3:17])=[N:12][CH:13]=[CH:14][C:15]=2[CH3:16])[OH:9])=[N:6][CH:7]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[O-]S([O-])(=S)=O.[Na+].[Na+].C([O-])(O)=O.[Na+]>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([N+:18]([O-:20])=[O:19])[C:5]([C:8]([C:10]2[C:11]([CH3:17])=[N:12][CH:13]=[CH:14][C:15]=2[CH3:16])=[O:9])=[N:6][CH:7]=1
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Komponenten

6

Edukt 4

HCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 57942234(5-Chloro-3-nitro-pyridin-2-yl)-(2,4-dimethyl-pyridin-3-yl)-methanol

Produkt 1

HCID 57942081(3-Nitro-5-chloro-pyridin-2-yl)-(2,4-dimethyl-pyridin-3-yl)-methanone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A mixture of (5-chloro-3-nitro-pyridin-2-yl)-(2,4-dimethyl-pyridin-3-yl)-methanol (1.46 g) and Dess-Martin periodinane (2.52 g, 5.91 mmol) in CH2Cl2 (15 mL) at room temperature was stirred for 5 h. A mixture of 10% aqueous Na2S2O3 (10 mL) and saturated aqueous NaHCO3 (10 mL) was then added and the biphasic mixture vigorously stirred for 30 min. The phases were then separated and the aqueous portion extracted with CH2Cl2. The combined organic extracts were washed with saturated aqueous NaHCO3, then brine, dried (Na2SO4) and filtered. The filtrate was concentrated under reduced pressure and the residue purified by flash column chromatography over silica gel to provide (5-chloro-3-nitro-pyridin-2-yl)-(2,4-dimethyl-pyridin-3-yl)-methanone. Mass spectrum m/z: 292.3 (M+Na).

Aufarbeitung

  1. additionwas then added
  2. stirringthe biphasic mixture vigorously stirred for 30 min
  3. customThe phases were then separated
  4. extractionthe aqueous portion extracted with CH2Cl2
  5. washThe combined organic extracts were washed with saturated aqueous NaHCO3
  6. dry with materialbrine, dried (Na2SO4)
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated under reduced pressure
  9. customthe residue purified by flash column chromatography over silica gel

Quellen und Nachweise

ORD-Eintrag
ord-cf871b5457ed4788b155fc85b9950ef4
Quelldatensatz
uspto-grants-2013_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08519135B2

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