Ethyl Acetate → (NE)-2-methyl-N-[(8-nitroquinolin-7-yl)methylidene]propane-2-sulfinamide

HRID 513648Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 513648
[N+:1]([C:4]1[C:5]([CH:14]=O)=[CH:6][CH:7]=[C:8]2[C:13]=1[N:12]=[CH:11][CH:10]=[CH:9]2)([O-:3])=[O:2].[CH3:16][C:17]([S:20]([NH2:22])=[O:21])([CH3:19])[CH3:18].CCOC(C)=O>C1COCC1.[Cl-].[Na+].O.[O-]CC.[O-]CC.[O-]CC.[O-]CC.[Ti+4]>[N+:1]([C:4]1[C:5](/[CH:14]=[N:22]/[S:20]([C:17]([CH3:19])([CH3:18])[CH3:16])=[O:21])=[CH:6][CH:7]=[C:8]2[C:13]=1[N:12]=[CH:11][CH:10]=[CH:9]2)([O-:3])=[O:2]

Komponenten

7

Edukt 3

HCID 8857Ethyl AcetateHCID 3382465Tert-ButanesulfinamideHCID 117695548-Nitro-7-quinolinecarboxaldehyde2×

Produkt 1

HCID 88861906(NE)-2-methyl-N-[(8-nitroquinolin-7-yl)methylidene]propane-2-sulfinamideAusbeute 76,5 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 76524Titanium tetraethoxideKatalysatorHCID 8028TetrahydrofuranLösungsmittelHCID 57417360Sodium chloride; waterLösungsmittel

Versuchsvorschrift

Titanium tetra-ethoxide (1.2 ml, 4.95 mmol) was added to a solution of 8-nitro-quinoline-7-carbaldehyde (Intermediate 204) (0.5 g, 2.47 mmol) and 2-methylpropane-2-sulfinamide (660 mg, 5.4 mmol) in THF (20 ml) under a nitrogen atmosphere and the mixture was heated under reflux for 17 h. The solution was cooled to room temperature and poured into rapidly stirring brine (40 ml) and stirred for 30 min. EtOAc (40 ml) was added and the mixture was filtered through Celite and washed with EtOAc (40 ml). The aqueous phase was extracted with EtOAc. The organic phases were dried (MgSO4) and concentrated in vacuo. The solid was purified by column chromatography using heptane/EtOAc (1:1) to give the title compound (577 mg, 76%). The compound could not be detected by HPLCMS therefore structure was confirmed by 1H NMR.

Aufarbeitung

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 17 h
  3. filtrationthe mixture was filtered through Celite
  4. washwashed with EtOAc (40 ml)
  5. extractionThe aqueous phase was extracted with EtOAc
  6. dry with materialThe organic phases were dried (MgSO4)
  7. concentrationconcentrated in vacuo
  8. customThe solid was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-142cec02e072477f8e345e8551841e26
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09102688B2

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