Reaktionsgleichung
[CH3:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6](N)[C:7]=1[C:8]([O:10][CH3:11])=[O:9].[ClH:13].N([O-])=O.[Na+].O.O.[Cl-].[S:21](=[O:23])=[O:22]>C(O)(=O)C.O>[Cl:13][S:21]([C:6]1[CH:5]=[CH:4][CH:3]=[C:2]([CH3:1])[C:7]=1[C:8]([O:10][CH3:11])=[O:9])(=[O:23])=[O:22]Komponenten
Edukt 5
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Reaktionsbedingungen
- Temperatur
- 0 °C
Versuchsvorschrift
The methyl 6-methylanthranilate so prepared (4.23 g, 0.026 mol) was dissolved in 25 ml of acetic acid and the solution cooled to 0° C. Concentrated hydrochloric acid (45 ml) was added to produce a tan slurry. A solution of 1.89 g (0.027 mol) of sodium nitrite in 8 ml water was added dropwise with stirring, the resulting orange solution was stirred at 0° C. for 1 hour and then added in 6 portions to a mixture of 2.18 g (0.013 mol) of cuptic chloride dihydrate and sulfur dioxide (6.3 g) in 33 ml of acetic acid and 6 ml of water at 0° C. The dark green solution was stirred at room temperature overnight, poured into 300 ml of ice-water, and the solid which separated was collected and dried by suction to provide 1.11 g of methyl 2-chlorosulfonyl-6-methylbenzoate which was immediately added to 100 ml of ice cold ammonium hydroxide and stirred at room temperature overnight. The solution was acidified to pH 1 with concentrated hydrochloric acid, and the resulting precipitate was collected and air-dried to provide 729 mg (12%) of 4-methylsaccharin, mp 224°-226° C.
Aufarbeitung
- customto produce a tan slurry
- stirringthe resulting orange solution was stirred at 0° C. for 1 hour
- stirringThe dark green solution was stirred at room temperature overnight
- customthe solid which separated
- customwas collected
- customdried by suction
Quellen und Nachweise
- ORD-Eintrag
- ord-0a4306bb8b90444f8364117aebdc5e80
- Quelldatensatz
- uspto-grants-1996_10
- Patentnummer
- US05563163
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