Diethyl Ether → 3-Ethyl-5-hexylsulfonamido-2-methylbenzoxazolium p-toluenesulfonate

HRID 344993

Reaktionsgleichung

[CH2:1]([S:7]([NH:10][C:11]1[CH:12]=[CH:13][C:14]2[O:18][C:17]([CH3:19])=[N:16][C:15]=2[CH:20]=1)(=[O:9])=[O:8])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[C:21]1([CH3:33])[CH:26]=[CH:25][C:24]([S:27]([O:30]CC)(=[O:29])=[O:28])=[CH:23][CH:22]=1.[CH2:34](OCC)[CH3:35]>CO>[C:21]1([CH3:33])[CH:22]=[CH:23][C:24]([S:27]([O-:30])(=[O:28])=[O:29])=[CH:25][CH:26]=1.[CH2:34]([N+:16]1[C:15]2[CH:20]=[C:11]([NH:10][S:7]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6])(=[O:9])=[O:8])[CH:12]=[CH:13][C:14]=2[O:18][C:17]=1[CH3:19])[CH3:35]

Komponenten

Reaktionsbedingungen

Temperatur: 150 °C

Versuchsvorschrift

A mixture of 60 grams (0.2 Mol) 5-hexylsulfonamido-2-methylbenzoxazole and 44 grams (0.22 Mol) ethyl p-toluenesulfonate was heated in a round bottom flask at 150° C. for 5 minutes. Upon cooling to room temperature the crude brown mass almost solidified. The product was dissolved in 25 mL methanol and poured into 300 mL diethyl ether with rapid stirring for one hour. The solid precipitate was chilled at 2° C. for 12 hours, then filtered. The tan powder was thoroughly washed with ether and recrystallized from 200 mL hot isopropyl alcohol to yield 23.4 grams (47 mMol, 23% yield) of white crystalline product, m.p.=159°-161° C.

Aufarbeitung

temperatureUpon cooling to room temperature the crude brown mass
temperatureThe solid precipitate was chilled at 2° C. for 12 hours
filtrationfiltered
washThe tan powder was thoroughly washed with ether
customrecrystallized from 200 mL hot isopropyl alcohol

Quellen und Nachweise

ORD-Eintrag: ord-3643c870cb7b4b4b897b06fdf136c84a
Quelldatensatz: uspto-grants-1991_10
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US05055387

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