Dimethyl Sulfoxide → HCID 131718401, compound

Participants

Reaction Steps

122.2 g (731 mmols) of p-nitrobenzoic acid, 11.3 g of dimethylsulfoxide, 2.0 g of a 5% platinum-supported catalyst, and 260 g of methanol were charged into a one liter autoclave, followed by filling hydrogen at a pressure of about 4 kg/cm2 and continuing agitation at room temperature until an equivalent of hydrogen was reacted with p-nitrobenzoic acid. After removal of the catalyst, 120.0 g (677 mmols) of 4-diethylaminobenzaldehyde, 30.0 g of acetic acid and 100 g of methanol were added to the resultant residue, followed by agitation at room temperature for 5 hours. After removal of the resultant crystals by filtration, they were washed with methanol to obtain yellow crystals and dried to isolate 187.6 g (yield 88.7%) of α-p-(diethylamino)phenyl]-N-(4-carboxyphenyl)nitrone with a purity of 96%. The thus obtained α-[p-(diethylamino)-phenyl]-N-(4-carboxyphenyl)nitrone had the following results with respect to mass spectra (MS), NMR spectra (NMR), IR spectra (IR) and elementary analysis.

Provenance & Evidence