Methyl 6-chloro-5-nitronicotinate → Ethyl 4-(5-(methoxycarbonyl)-3-nitropyridin-2-yl)thiomorpholine-3-carboxylate

HRID 69653

Reaktionsgleichung

Reaktionsgleichung von HRID 69653
Cl[C:2]1[C:11]([N+:12]([O-:14])=[O:13])=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][N:3]=1.[NH:15]1[CH2:20][CH2:19][S:18][CH2:17][CH:16]1[C:21]([O:23][CH2:24][CH3:25])=[O:22]>ClCCl>[CH3:9][O:8][C:6]([C:5]1[CH:10]=[C:11]([N+:12]([O-:14])=[O:13])[C:2]([N:15]2[CH2:20][CH2:19][S:18][CH2:17][CH:16]2[C:21]([O:23][CH2:24][CH3:25])=[O:22])=[N:3][CH:4]=1)=[O:7]

Komponenten

4

Edukt 2

HCID 346961Methyl 6-chloro-5-nitronicotinateHCID 13604869Ethyl thiomorpholine-3-carboxylate

Produkt 1

HCID 58324448Ethyl 4-(5-(methoxycarbonyl)-3-nitropyridin-2-yl)thiomorpholine-3-carboxylateAusbeute 95 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Methyl 6-chloro-5-nitronicotinate (1.1 g, 5.10 mmol) was added to ethyl thiomorpholine-3-carboxylate (2.0 g, 11.41 mmol) neat while stirring at room temperature. The viscous yellow reaction was heated to 90° C. for one hour and then allowed to cool back to room temperature. The reaction was diluted with dichloromethane (20 mL) and purified via column chromatography (220 g SiO2, 20-30% gradient, ethyl acetate in hexanes) to yield the title compound (1.71 g, 95%) as a yellow oil. [M+H] calc'd for C15H18N2O6S, 356; found, 356.

Aufarbeitung

  1. customThe viscous yellow reaction
  2. temperaturewas heated to 90° C. for one hour
  3. temperatureto cool back to room temperature
  4. custompurified via column chromatography (220 g SiO2, 20-30% gradient, ethyl acetate in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-2e44c9b0eb6d4d6dbf6b6b11b8f2d14e
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08822470B2

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