(Diethylamino)sulfur trifluoride → HCID 20189398, Verbindung

HRID 1789029Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1789029
O[CH2:2][C:3]1[NH:4][C:5]([CH3:28])=[C:6]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH:7]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([N+:20]([O-:22])=[O:21])[CH:15]=2)[C:8]=1[C:9]([O:11][CH2:12][CH3:13])=[O:10].C(N(S(F)(F)[F:35])CC)C.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[F:35][CH2:2][C:3]1[NH:4][C:5]([CH3:28])=[C:6]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH:7]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([N+:20]([O-:22])=[O:21])[CH:15]=2)[C:8]=1[C:9]([O:11][CH2:12][CH3:13])=[O:10]

Komponenten

5

Edukt 3

HCID 123472(Diethylamino)sulfur trifluorideHCID 173874FR 7534HCID 516892Sodium Bicarbonate

Produkt 1

HCID 20189398HCID 20189398, VerbindungAusbeute 15,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

Diethyl 1,4-dihydro-2-(hydroxymethyl)-6-methyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylate (0.1 g, 0.25 mmoles) in dry methylene chloride (5 ml) was added to a stirred solution at -60° of diethylaminosulphur trifluoride (0.068 ml, 0.55 mmoles) in dry methylene chloride (10 ml) over 10 minutes. The reaction mixture was allowed to reach room temperature over 2.5 hours, poured into aqeuous sodium bicarbonate (15 ml) and the aqueous layer extracted with methylene chloride (2×). The organic extracts were washed with water, dried (MgSO4) and the solvent was evaporated. The residue was chromatographed on silica eluting with ethyl acetate/methylene chloride mixtures to give the title compound (0.015 g); identical with that prepared in Example 94.

Aufarbeitung

  1. extractionthe aqueous layer extracted with methylene chloride (2×)
  2. washThe organic extracts were washed with water
  3. dry with materialdried (MgSO4)
  4. customthe solvent was evaporated
  5. customThe residue was chromatographed on silica eluting with ethyl acetate/methylene chloride

Quellen und Nachweise

ORD-Eintrag
ord-22f4db88423c4398b127f4bc8242b287
Quelldatensatz
uspto-grants-1987_08
Patentnummer
US04686217

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