Hydrochloric Acid → 5-Nitro-2-p-tolylbenzo[d]thiazole

HRID 1886943

Reaktionsgleichung

O.O.O.O.O.O.O.O.O.[S-2:10].[Na+].[Na+].[S].Cl[C:15]1[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][C:16]=1[NH:24][C:25](=O)[C:26]1[CH:31]=[CH:30][C:29]([CH3:32])=[CH:28][CH:27]=1.Cl>C(O)C.O>[N+:21]([C:18]1[CH:19]=[CH:20][C:15]2[S:10][C:25]([C:26]3[CH:31]=[CH:30][C:29]([CH3:32])=[CH:28][CH:27]=3)=[N:24][C:16]=2[CH:17]=1)([O-:23])=[O:22]

Komponenten

Reaktionsbedingungen

Temperatur: 85 °C

Versuchsvorschrift

Sodium sulfide nonahydrate (875 mg, 3.78 mmol) and sulfur (120 mg, 3.78 mmol) were heated until molten. The water was driven off with nitrogen to give a solid. The obtained solid was added in portions to N-(2-chloro-5-nitrophenyl)-4-methylbenzamide (1 g, 3.44 mmol) in ethanol (20 mL) at 85° C. The solution was stirred at 85° C. for 3 h. After cooling, 2M aqueous HCl was added, and the solution was extracted three times with ethyl acetate. The combined organic layers were dried over anhydrous MgSO4 and evaporated. The resulting solid was purified by column chromatography eluting with ethyl acetate/hexanes 10:90 v/v to afford 400 mg (43%) of the title compound.

Aufarbeitung

customto give a solid
temperatureAfter cooling
extractionthe solution was extracted three times with ethyl acetate
dry with materialThe combined organic layers were dried over anhydrous MgSO4
customevaporated
customThe resulting solid was purified by column chromatography
washeluting with ethyl acetate/hexanes 10:90 v/v

Quellen und Nachweise

ORD-Eintrag: ord-92cee1e69dff4d2c816103ea4cdda82f
Quelldatensatz: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08501713B2

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