Tert-Butanesulfinamide → HCID 86689260, Verbindung

HRID 1409520Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1409520
[Br:1][C:2]1[CH:3]=[C:4]2[C:14](=[CH:15][CH:16]=1)[O:13][C:7]1[CH:8]=[N:9][C:10]([Cl:12])=[CH:11][C:6]=1[C:5]2=O.[CH3:18][C:19]([S:22]([NH2:24])=[O:23])([CH3:21])[CH3:20]>C1COCC1.[Cl-].[Na+].O.[O-]CC.[Ti+4].[O-]CC.[O-]CC.[O-]CC>[Br:1][C:2]1[CH:3]=[C:4]2[C:14](=[CH:15][CH:16]=1)[O:13][C:7]1[CH:8]=[N:9][C:10]([Cl:12])=[CH:11][C:6]=1[C:5]2=[N:24][S:22]([C:19]([CH3:21])([CH3:20])[CH3:18])=[O:23]

Komponenten

6

Edukt 2

HCID 3382465Tert-ButanesulfinamideHCID 574756367-Bromo-3-chloro-5H-chromeno[2,3-c]pyridin-5-one

Produkt 1

HCID 86689260HCID 86689260, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 76524Titanium tetraethoxideKatalysatorHCID 8028TetrahydrofuranLösungsmittelHCID 57417360Sodium chloride; waterLösungsmittel

Reaktionsbedingungen

Temperatur
75 °C

Versuchsvorschrift

A mixture of 7-bromo-3-chloro-5H-chromeno[2,3-c]pyridin-5-one (20 g, 64.4 mmol), 2-methyl-2-propanesulfinamide (23.42 g, 193 mmol) and titanium (IV) ethoxide (45.3 mL, 219 mmol) in dry THF 250 mL was heated at 75° C. overnight. The mixture was cooled to RT, then brine was added while stirring. The resulting suspension was filtered through celite, and the solid was washed with EtOAc. The filtrate was washed with brine, dried over sodium sulfate and concentrated. The crude material was purified by column chromatography with gradient of 0-30% EtOAc/Hexane to give the desired product as an orange solid. MS m/z=415.0 [M+H]+.

Aufarbeitung

  1. temperatureThe mixture was cooled to RT
  2. filtrationThe resulting suspension was filtered through celite
  3. washthe solid was washed with EtOAc
  4. washThe filtrate was washed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. customThe crude material was purified by column chromatography with gradient of 0-30% EtOAc/Hexane

Quellen und Nachweise

ORD-Eintrag
ord-dc647cd6208e461e8933ff46b8d5dc64
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08921363B2

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