Water → HCID 18670322, Verbindung

HRID 1059406

Reaktionsgleichung

Reaktionsgleichung von HRID 1059406
[CH3:1][O:2][CH2:3][N:4]1[C:9]2[CH:10]=[C:11]([C:14]([C:17]3[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=3)(O)[CH3:15])[CH:12]=[CH:13][C:8]=2[S:7][C:6]2[N:23]=[CH:24][CH:25]=[N:26][C:5]1=2.ClS(OC)(=O)=O.O.C(OCC)(=O)C>ClCCl>[N:19]1[CH:20]=[CH:21][CH:22]=[C:17]([C:14]([C:11]2[CH:12]=[CH:13][C:8]3[S:7][C:6]4[N:23]=[CH:24][CH:25]=[N:26][C:5]=4[N:4]([CH2:3][O:2][CH3:1])[C:9]=3[CH:10]=2)=[CH2:15])[CH:18]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 69938Methyl chlorosulphateHCID 18670441HCID 18670441, Verbindung

Produkt 1

HCID 18670322HCID 18670322, VerbindungAusbeute 79,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 303 mg of 1-(10-methoxymethyl-10H-pyrazino[2,3-b][1,4]benzothiazin-8-yl)1-(pyridin-3-yl)ethanol in dichloromethane was added in a nitrogen atmosphere 0.32 ml of methyl chlorosulfonate and the resulting mixture was heated under reflux for 2 hours. Then the reaction mixture was brought back to room temperature and distributed into water and ethyl acetate. The extract was dried over anhydrous magnesium sulfate and filtered. After distilling off the solvent under reduced pressure, the residue was purified by silica gel column chromatography (eluted with dichloromethane/methanol) to thereby give 230 mg of the title compound as a yellow solid.

Aufarbeitung

  1. temperaturethe resulting mixture was heated
  2. temperatureunder reflux for 2 hours
  3. customwas brought back to room temperature
  4. dry with materialThe extract was dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. distillationAfter distilling off the solvent under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (eluted with dichloromethane/methanol)

Quellen und Nachweise

ORD-Eintrag
ord-03dc200643aa4ec2bda2b17c98c9faf0
Quelldatensatz
uspto-grants-2003_02
Patentnummer
US06518423B1

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