Benzoyl chloride → N-[2-[2-(4-Oxo-4H-1,3-benzothiazin-2-yl)-4-pyridyl]ethyl]benzamide

HRID 748312Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 748312
FC(F)(F)C(O)=O.[NH2:8][CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][N:14]=[C:13]([C:17]2[S:18][C:19]3[CH:27]=[CH:26][CH:25]=[CH:24][C:20]=3[C:21](=[O:23])[N:22]=2)[CH:12]=1.[C:28](Cl)(=[O:35])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>CN(C)C(=O)C.O>[O:23]=[C:21]1[C:20]2[CH:24]=[CH:25][CH:26]=[CH:27][C:19]=2[S:18][C:17]([C:13]2[CH:12]=[C:11]([CH2:10][CH2:9][NH:8][C:28](=[O:35])[C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[CH:16]=[CH:15][N:14]=2)=[N:22]1

Komponenten

7

Edukt 4

HCID 7412Benzoyl chlorideHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 684561462-[4-(2-Aminoethyl)-2-pyridyl]-4h-1,3-benzothiazine-4-one trifluoroacetic acid salt

Produkt 1

HCID 59750348N-[2-[2-(4-Oxo-4H-1,3-benzothiazin-2-yl)-4-pyridyl]ethyl]benzamideAusbeute 36,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 31374DimethylacetamideLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

2-[4-(2-Aminoethyl)-2-pyridyl]-4H-1,3-benzothiazine-4-one trifluoroacetic acid salt (0.50 g, 1.2 mmol) was dissolved in N,N-dimethylacetamide (10 ml), and benzoyl chloride (0.36 g, 2.6 mmol) and potassium carbonate (0.17 g, 1.2 mmol) were added thereto. The reaction mixture was stirred at 60° C. for 5 hrs, combined with ethyl acetate and water. The organic layer was successively washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated, and the residue was subjected to a silica gel column chromatography. The fractions eluted with methanol-ethyl acetate (1:20, v/v) were collected, concentrated and recrystallized from hexane-chloroform to give the titled compound (0.17 g, 36%) as white crystals.

Aufarbeitung

  1. washThe organic layer was successively washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customThe solvent was evaporated
  4. washThe fractions eluted with methanol-ethyl acetate (1:20
  5. customv/v) were collected
  6. concentrationconcentrated
  7. customrecrystallized from hexane-chloroform

Quellen und Nachweise

ORD-Eintrag
ord-21501fa3ef4e46939bc2849279616bc4
Quelldatensatz
uspto-grants-2008_07
Patentnummer
US07399759B2

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