Azo compounds and process for production thereof

C - Chemistry – Metallurgy – 07 – D

Patent

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C07D 307/79 (2006.01) C07D 405/04 (2006.01)

Patent

CA 2576063

A process for the production of an aromatic azo compound having a 2,3- dihydrobenzofuran ring bearing a diazo group at the 5-position of the ring by conducting the diazo coupling of a 2,3-dihydrobenzofuran derivative represented by the general formula (II): (II) [wherein R1 and R2 are each independently C1-6 alkyl; R3 is optionally substituted aryl; and R4, R5 and R6 are each independently hydrogen, C1-6 alkyl, halogeno, C1-6 alkoxy, or C1-6 alkylthio] with a benzenediazonium salt having an electron-withdrawing group at the p- and/or o-position in a mixed solvent composed of water and a polar organic solvent.

Cette invention concerne un procédé de production d~un composé azoïque aromatique ayant un cycle 2,3-dihydrobenzofurane supportant un groupe diazoïque en position 5 du cycle en menant la liaison diazoïque d~un dérivé 2,3-dihydrobenzofuran représenté par la formule générale (II) : (II) [où R1 et R2 représentent chacun de façon indépendante un alkyl C1-6 ; R3 est facultativement un aryle substitué ; et R4, R5 et R6 représentent chacun de façon indépendante un hydrogène, un alkyl C1-6, un halogéno, un alcoxy C1-6, ou un alkylthio C1-6] avec un sel de benzènediazonium ayant un groupe accepteur d~électrons en position p et/ou o, dans un mélange de solvants composé d~eau et un solvant organique polaire.

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