Methyl iodide → 5-Chloro-2-(methylthio)benzothiazole

HRID 344709

Reaktionsgleichung

Reaktionsgleichung von HRID 344709
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][C:8]([SH:10])=[N:7][C:6]=2[CH:11]=1.[OH-].[Na+].I[CH3:15]>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][C:8]([S:10][CH3:15])=[N:7][C:6]=2[CH:11]=1

Komponenten

5

Edukt 3

HCID 6328Methyl iodideHCID 14798Sodium HydroxideHCID 178527796HCID 178527796, Verbindung

Produkt 1

HCID 6457465-Chloro-2-(methylthio)benzothiazoleAusbeute 98,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

With stirring under ice cooling, 2.00 g (9.92 mmols) of 5-chloro-2-mercaptobenzothiazole was added gradually to 10 ml of a solution of 0.24 g (10.00 mmols) of sodium hydroxide in dimethylformamide (DMF). The mixture was dropwise added to 20 ml of a solution of 0.62 ml (9.96 mmols) of iodomethane in 20 ml of DMF with stirring under ice cooling and the mixture was stirred for further 30 minutes under ice cooling. The mixture was concentrated under reduced pressure, and to the residue was added an aqueous saturated sodium bicarbonate followed by extraction of the solution with chloroform. The chloroform layer was dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: chloroform/methanol =100/1) to afford 2.10 g (yield: 98%) of 5-chloro-2-methylthiobenzothiazole.

Aufarbeitung

  1. stirringwith stirring under ice cooling
  2. stirringthe mixture was stirred for further 30 minutes under ice cooling
  3. concentrationThe mixture was concentrated under reduced pressure
  4. additionto the residue was added an aqueous saturated sodium bicarbonate
  5. extractionfollowed by extraction of the solution with chloroform
  6. dry with materialThe chloroform layer was dried over anhydrous sodium sulfate
  7. customThe solvent was evaporated under reduced pressure
  8. customthe residue was purified by silica gel column chromatography (eluent: chloroform/methanol =100/1)

Quellen und Nachweise

ORD-Eintrag
ord-042dce2aab6841d0a8823b8c8bcc9c6c
Quelldatensatz
uspto-grants-1991_10
Patentnummer
US05053408

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