Promethazine Hydrochloride → Thiazinamium Metilsulfate

HRID 839902

Reaction equation

HRID 839902 reaction equation
[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

Participants

4

Reactant 2

HCID 6014Promethazine HydrochlorideHCID 6497Dimethyl Sulfate2×

Product 1

HCID 6015Thiazinamium Metilsulfate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-bec2f61d3bcb4d9a9934737b21c253d8
Source dataset
uspto-grants-1978_06
Patent number
US04097596

Linked notes

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