91361-37-4

Basic information

• Product Name: 2-Furancarboxamide, tetrahydro-N-(4-methylphenyl)-3-[[(4-nitrophenyl)amino]phenylmethylene ]-4,5-dioxo-2-phenyl-, (E)-
• CAS NO: 91361-37-4
• Molecular Formula: C31H23N3O6
• Mol File: 91361-37-4.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 2-Furancarboxamide, tetrahydro-N-(4-methylphenyl)-3-[[(4-nitrophenyl)amino]phenylmethylene ]-4,5-dioxo-2-phenyl-, (E)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Furancarboxamide, tetrahydro-N-(4-methylphenyl)-3-[[(4-nitrophenyl)amino]phenylmethylene ]-4,5-dioxo-2-phenyl-, (E)-(91361-37-4)
• EPA Substance Registry System: 2-Furancarboxamide, tetrahydro-N-(4-methylphenyl)-3-[[(4-nitrophenyl)amino]phenylmethylene ]-4,5-dioxo-2-phenyl-, (E)-(91361-37-4)

Safety Data

• Hazardous Substances Data: 91361-37-4(Hazardous Substances Data)

Upstream product

• 17571-17-4 4-benzoyl-5-phenyl-furan-2,3-dione 
• 7175-47-5 4-methylphenyl isocyanide 
• 100-01-6 4-nitro-aniline 
• 91361-18-1 5,6a-Dihydro-5-(4-methylphenylimino)-4,6a-diphenylfuro<2,3-b>furan-2,3-dion 

Relevant articles and documents

Structures of the 1:1 Adducts of Aryl Isocyanides to 4-Benzoyl-5-phenylfuran-2,3-dione and Their Products with Nucleophiles.-Novel Rearrangements of 5,5-Disubstituted 4-Methylenefuran-2,3-diones

The structures of the previously reported 1:1 adducts of the furan-2,3-dione 8 and aryl isocyanides 2 and their products with nucleophiles are reassigned with the aid of X-ray diffraction, carbon-13 NMR, and mass spectra.Accordingly, the 1:1 adducts of 8 and 2 possess the furofuran-2,3-dione structure 14.In the reaction of the furofuran-2,3-diones 14a,b with alcohols, phenol, or carboxylic acid the O-6-C-6a bond is opened affording the furan-2,3-diones 16-21.The phenol product 19b (C31H23NO5) crystallizes monoclinically in the space group C2/c with eight molecules per cell.On N-acetylation of the butanol products 18 a rearrangement via acyclic intermediates occurs producing the furan-2,3-diones 22.The intermediate butoxy compound 22b is solvolyzed in methanol yielding the methoxy compound 23b.Hydrolysis of the rearranged acetylation products 22a,b and of the non-rearranged acetic acid product 20b as well as attempts to acetylate the nitrogen atom of the alcohol products 16a, 17a, of the phenol product 19a, and of the carboxylic acid products 20a,21a afforded the stable pyrrole-2,5-diones 26a and b,respectively, with concomittant decarboxylation.The pyrroledione 26b (C26H21NO4) crystallizes monoclinically in the space group P21/a with four molecules per cell.The furofuran-2,3-diones 14 react with 2- and 4-nitroaniline under opening of the O-6-C-6a bond and subsequent furandione-furandione rearrangement affording 28a,b and 28c,d, respectively.The furan-2,3-dione 28b (C31H23N3O6) crystallizes triclinically in the space group P1 with two molecules per cell.In contrast to hydroxy compounds and nitroanilines, aniline and water attack the lactone group of14a,b yielding as the final products the pyrrole derivatives 31a,b and the furan derivatives 32a,b, respectively.The mechanisms of the various rearrangements and the principle of the furandione-furandione isomerization are discussed.