Water → 2-Methanesulfonyloxyimino-4-p-tolyl-but-3-enenitrile
Reaktionsgleichung
[OH:1][N:2]=[C:3]([CH:6]=[CH:7][C:8]1[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=1)[C:4]#[N:5].[CH3:15][S:16](Cl)(=[O:18])=[O:17].C(N(CC)CC)C.O>O1CCCC1>[CH3:15][S:16]([O:1][N:2]=[C:3]([CH:6]=[CH:7][C:8]1[CH:9]=[CH:10][C:11]([CH3:14])=[CH:12][CH:13]=1)[C:4]#[N:5])(=[O:18])=[O:17]Komponenten
Reaktionsbedingungen
- Temperatur
- 0 °C
Versuchsvorschrift
2-Hydroxyimino-4-p-tolyl-but-3-enenitrile (1.9 g; 0.01 mol) is dissolved in 15 ml of anhydrous tetrahydrofuran, and cooled to 0° C. Methanesulfonyl chloride (0.93 ml, 0.012 mol) is added at once, followed by triethylamine (2.1 ml, 0.015 mol) dropwise over 20 min, keeping the temperature of the mixture below 5° C. The mixture is then stirred at 5-10° C. for 3.5 hours, and poured into 200 ml of iced water. The suspension is extracted with ethyl acetate, the organic extract is washed neutral with water, then with brine, and dried over magnesium sulfate. Rotary evaporation of the solvent and recrystallization from 50 ml of ethanol yields 2-methanesulfonyloxyimino-4-p-tolyl-but-3-enenitrile (1.7 g; 64%) as off-white crystals, mp 134-135° C. with one part melting at 145° C. 1H-NMR reveals the presence of two isomers (probably E/Z around the imino double bond).
Aufarbeitung
- customthe temperature of the mixture below 5° C
- extractionThe suspension is extracted with ethyl acetate
- extractionthe organic extract
- washis washed neutral with water
- dry with materialwith brine, and dried over magnesium sulfate
- customRotary evaporation of the solvent and recrystallization from 50 ml of ethanol
Quellen und Nachweise
- ORD-Eintrag
- ord-58d073c768784635b9455ee81640d83b
- Quelldatensatz
- uspto-grants-2004_03
- Patentnummer
- US06703182B1
Notizen zur Reaktion
Wird geladen…