p-Toluenesulfonic acid → HCID 178498286, Verbindung

HRID 349501

Reaktionsgleichung

C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH3:12][O:13][C:14](=[O:24])[C:15]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[C:17]([NH2:23])[CH:16]=1.[N+:25]([C:28]1[CH:35]=[CH:34][C:31]([C:32]#[N:33])=[CH:30][CH:29]=1)([O-:27])=[O:26].C([O-])(O)=O.[Na+]>C1C=CC=CC=1>[CH3:12][O:13][C:14](=[O:24])[C:15]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[C:17]([NH:23][C:32](=[NH:33])[C:31]2[CH:30]=[CH:29][C:28]([N+:25]([O-:27])=[O:26])=[CH:35][CH:34]=2)[CH:16]=1

Komponenten

Reaktionsbedingungen

Temperatur: 160 °C

Versuchsvorschrift

Anhydrous p-toluenesulfonic acid (6.30 g, 33.1 mmol) was added to 50 ml of benzene and the resulting mixture was refluxed while removing water using a dean-stock trap. Added thereto were 3-amino-4-methoxy benzoic acid methyl ester (3 g, 16.6 mmol) obtained in step 1 of Preparation Example 1 and 4-nitrobenzonitrile (2.94 g, 19.9 mol), followed by stirring at 160° C. for 8 hours. The resulting solution was cooled to room temperature, the reaction was stopped by adding NaHCO3 thereto, extracted with ethyl acetate, the extract was dried over MgSO4 and concentrated under a reduced pressure. The resulting residue was purified by silica gel column chromatography to obtain the title compound (2.83 g, 8.59 mmol) in a yield of 52%.

Aufarbeitung

temperaturethe resulting mixture was refluxed
customwhile removing water using a dean-stock trap
additionAdded
temperatureThe resulting solution was cooled to room temperature
extractionextracted with ethyl acetate
dry with materialthe extract was dried over MgSO4
concentrationconcentrated under a reduced pressure
customThe resulting residue was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag: ord-f8eccf94540f43b9aff3eaedff7b2137
Quelldatensatz: uspto-grants-2007_02
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07179832B2

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