Diisopropyl Ether → 4-(N-methylacetamido)benzene-1-sulfonyl chloride

HRID 260881

Reaktionsgleichung

[CH3:1][N:2]([C:9](=[O:11])[CH3:10])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[Cl:12][S:13](O)(=[O:15])=[O:14].C(OC(C)C)(C)C>CCCCCC>[C:9]([N:2]([C:3]1[CH:8]=[CH:7][C:6]([S:13]([Cl:12])(=[O:15])=[O:14])=[CH:5][CH:4]=1)[CH3:1])(=[O:11])[CH3:10]

Komponenten

Reaktionsbedingungen

Temperatur: 80 °C

Versuchsvorschrift

N-Methylacetanilide (25.0 g, 188.0 mmol) was added to chlorosulfonic acid (62.8 ml) under cooling with ice in portions at such a rate as not to raise the temperature of the resulting mixture to 50° C. or above, which took about 10 minutes. The obtained mixture was stirred at 80° C. for 2.5 hours and poured into a mixture comprising ice (200 ml), hexane (30 ml) and isopropyl ether (30 ml) under cooling with ice at 20° C. or below in portions to decompose excess chlorosulfonic acid. The precipitated crystal was recovered by filtration, washed with water and dissolved in ethyl acetate. The obtained solution was washed with water and a saturated aqueous solution of common salt. The organic layer was dried over magnesium sulfate and concentrated to give the title compound as a white crystal (19.4 g, yield: 42%).

Aufarbeitung

temperatureunder cooling with ice in portions at such a rate as not
temperatureto raise the temperature of the resulting mixture to 50° C. or above
temperatureunder cooling with ice at 20° C. or below in portions
filtrationThe precipitated crystal was recovered by filtration
washwashed with water
dissolutiondissolved in ethyl acetate
washThe obtained solution was washed with water
dry with materialThe organic layer was dried over magnesium sulfate
concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag: ord-21aed41447f044a99ae1569d431f5828
Quelldatensatz: uspto-grants-1996_06
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US05530118

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