Thiomorpholine → 4-(5-Nitro-2-pyridinyl)thiomorpholine

HRID 22642

Reaktionsgleichung

Reaktionsgleichung von HRID 22642
Cl[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1.[NH:11]1[CH2:16][CH2:15][S:14][CH2:13][CH2:12]1>O1CCCC1>[N+:8]([C:5]1[CH:6]=[CH:7][C:2]([N:11]2[CH2:16][CH2:15][S:14][CH2:13][CH2:12]2)=[N:3][CH:4]=1)([O-:10])=[O:9]

Komponenten

4

Edukt 2

HCID 67164ThiomorpholineHCID 783082-Chloro-5-nitropyridine

Produkt 1

HCID 27984524-(5-Nitro-2-pyridinyl)thiomorpholine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 20 g (126 mmol) of 2-chloro-5-nitropyridine in 200 ml tetrahydrofuran were added dropwise 32.5 ml (315 mmol) thiomorpholine within 10 min. The reaction mixture was refluxed for additional 2 h. After cooling to room temperature, the solvent was removed in vacuo and the residue was re-dissolved in 200 ml ethyl acetate. The organic phase was washed with 200 ml 1 N sodium bicarbonate solution, dried (magnesium sulfate) and evaporated to give 29.3 g (quantitative) of the title compound as a yellow solid.

Aufarbeitung

  1. temperatureThe reaction mixture was refluxed for additional 2 h
  2. customthe solvent was removed in vacuo
  3. dissolutionthe residue was re-dissolved in 200 ml ethyl acetate
  4. washThe organic phase was washed with 200 ml 1 N sodium bicarbonate solution
  5. dry with materialdried (magnesium sulfate)
  6. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-0a6d260271f0483bbbb1796c2958fed9
Quelldatensatz
uspto-grants-2005_02
Patentnummer
US06849624B2

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