Promethazine Hydrochloride → Thiazinamium Metilsulfate

HRID 839902

Reaktionsgleichung

Reaktionsgleichung von HRID 839902
[CH3:1][CH:2]([N:18]([CH3:20])[CH3:19])[CH2:3][N:4]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[S:11][C:10]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]1=2.Cl.[S:22]([O:27]C)([O:25][CH3:26])(=[O:24])=[O:23]>CC(C)=O>[CH3:26][O:25][S:22]([O-:27])(=[O:24])=[O:23].[CH3:20][N+:18]([CH3:26])([CH3:19])[CH:2]([CH3:1])[CH2:3][N:4]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:10]=2[S:11][C:12]2[C:13]1=[CH:14][CH:15]=[CH:16][CH:17]=2

Komponenten

4

Edukt 2

HCID 6014Promethazine HydrochlorideHCID 6497Dimethyl Sulfate2×

Produkt 1

HCID 6015Thiazinamium Metilsulfate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

dl-Promethazine hydrochloride (30 g.) was converted to the free base and was dissolved in absolute acetone and dimethyl sulfate (10 g.) was added (this is less than are equivalent of dimethyl sulfate due to its hazardous nature). After standing overnight, the solution was heated on a steam bath and cooled. The precipitated solid was filtered, washed with tetrahydrofuran and ether to provide dl-trimethyl[1-methyl-2-(phenothiazine-10-yl)ethyl]ammonium methyl sulfate, 27.6 g., m.p. 170°-173° C.

Aufarbeitung

  1. temperaturethe solution was heated on a steam bath
  2. temperaturecooled
  3. filtrationThe precipitated solid was filtered
  4. washwashed with tetrahydrofuran and ether

Quellen und Nachweise

ORD-Eintrag
ord-bec2f61d3bcb4d9a9934737b21c253d8
Quelldatensatz
uspto-grants-1978_06
Patentnummer
US04097596

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