p-Toluidine → 4-Fluoro-N-(4-methylphenyl)benzenesulfonamide
Reaktionsgleichung
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][CH:3]=1.[F:9][C:10]1[CH:15]=[CH:14][C:13]([S:16](Cl)(=[O:18])=[O:17])=[CH:12][CH:11]=1>N1C=CC=CC=1>[F:9][C:10]1[CH:15]=[CH:14][C:13]([S:16]([NH:1][C:2]2[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][CH:3]=2)(=[O:18])=[O:17])=[CH:12][CH:11]=1Komponenten
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 0 °C
Versuchsvorschrift
4-Toluidine (6.430 g, 60 mmol) was dissolved in pyridine (200 mL). The resulting mixture was cooled down to 0° C. 4-fluoro-benzenesulfonyl chloride (7.784 g, 40 mmol) was added in portions. The mixture was stirred between 0° C. and room temperature overnight. Solvents were evaporated to dryness. The crude oil was dissolved in ethyl acetate (150 mL) and washed with 10% HCl (2×75 mL) and brine (1×75 mL). Organic phase was dried over magnesium sulfate before filtering and removal of solvent. The resulting solid was recrystallized in cyclohexane/ethyl acetate 9:1. The desired product, e.g. 4-fluoro-N-(4-methylphenyl)benzenesulfonamide (9.4754 g, 89%), was obtained as a colorless solid, in 98% purity by HPLC (MaxPlot detection between 230 and 400 nm).
Aufarbeitung
- customSolvents were evaporated to dryness
- dissolutionThe crude oil was dissolved in ethyl acetate (150 mL)
- washwashed with 10% HCl (2×75 mL) and brine (1×75 mL)
- dry with materialOrganic phase was dried over magnesium sulfate
- filtrationbefore filtering
- customremoval of solvent
- customThe resulting solid was recrystallized in cyclohexane/ethyl acetate 9:1
Quellen und Nachweise
- ORD-Eintrag
- ord-8912cf9b3f604e29935083c8d18147d1
- Quelldatensatz
- uspto-grants-2007_12
- Patentnummer
- US07312358B2
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