Potassium Carbonate → 2,6-dimethylthieno[2,3-b][1,5]benzoxazepin-4(5H)-one

HRID 1281873Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1281873
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[NH:9][C:10]([C:12]1[CH:16]=[C:15]([CH3:17])[S:14][C:13]=1Br)=[O:11].C(=O)([O-])[O-].[K+].[K+]>CS(C)=O>[CH3:17][C:15]1[S:14][C:13]2[O:1][C:2]3[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=3[NH:9][C:10](=[O:11])[C:12]=2[CH:16]=1

Komponenten

4

Edukt 2

HCID 11430Potassium CarbonateHCID 11110188N-(2-hydroxy-6-methylphenyl)-2-bromo-5-methyl-3-thiophenecarboxamide

Produkt 1

HCID 111182992,6-dimethylthieno[2,3-b][1,5]benzoxazepin-4(5H)-oneAusbeute 31 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Reaktionsbedingungen

Temperatur
145 °C

Versuchsvorschrift

To a solution of N-(2-hydroxy-6-methylphenyl)-2-bromo-5-methyl-3-thiophenecarboxamide (3.0 g) in dimethyl sulfoxide (25 ml) was added potassium carbonate (2.5 g), and the mixture was stirred at 145° C. for 2 hours. The reaction system was cooled to room temperature and poured into ice water. The precipitated crystals were collected by filtration and the filtrate was extracted with chloroform, washed twice with water, and dried over sodium sulfate. The solvent was evaporated under reduced pressure and the residue and the crystals obtained earlier were purified by silica gel column chromatography (chloroform:methanol=20:0-20:1). The obtained solid was collected by filtration from diisopropyl ether-hexane to give 2,6-dimethylthieno[2,3-b][1,5]benzoxazepin-4(5H)-one (700 mg).

Aufarbeitung

  1. temperatureThe reaction system was cooled to room temperature
  2. filtrationThe precipitated crystals were collected by filtration
  3. extractionthe filtrate was extracted with chloroform
  4. washwashed twice with water
  5. dry with materialdried over sodium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customthe residue and the crystals obtained earlier
  8. customwere purified by silica gel column chromatography (chloroform:methanol=20:0-20:1)
  9. filtrationThe obtained solid was collected by filtration from diisopropyl ether-hexane

Quellen und Nachweise

ORD-Eintrag
ord-1c5e06df86964166afd92dbc39c17fd1
Quelldatensatz
uspto-grants-2002_09
Patentnummer
US06455521B1

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