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

HRID 344993

Reaction equation

[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]

Participants

Conditions

Temperature: 150 °C

Procedure

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.

Workup

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

Sources & evidence

ORD record: ord-3643c870cb7b4b4b897b06fdf136c84a
Source dataset: uspto-grants-1991_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05055387

Linked notes

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