Process for the manufacture of iodine substituted benzonitriles with a linkage of the phenol ether type

摘要

275,213. Chemische Fabrik auf Actien, vorm. E. Schering. Aug. 2, 1926, [Convention date]. Iodo derivatives of cyanophenolethers having the constitution R-O-R1-CN, in which R and R1 represent iodo-substituted aryl residues, are prepared by condensing iodophenolethers with metallic salts of iodo-oxybenzonitriles or metallic salts of iodophenolethers with iodobenzonitriles. The iodobenzonitrile mav be replaced by an iodonitrobenzene, and the condensation product then reduced and treated after diazotization with copper cyanide. The condensation is effected by heating to, say, 210-240‹ C. in the presence of copper as catalyst. The products are useful as intermediates for the manufacture of pharmaceutical preparations. Examples are given of the preparation of 4-(41-methoxy-31-iodophenoxy)- 3 : 5-diiodo-1-cyanobenzene by condensing 2: 4- diiodoanisol with the potassium salt of 3: 5- diiodo-4-oxybenzonitrile and by condensing the potassium salt of o-iodomethylether of hydroquinone with 3: 4: 5-triiodo-1-benzonitrile. The Specification as open to inspection under Sect. 91 (3) (a) is not restricted to copper as catalyst, and states that the iodo-oxybenzonitrile may be replaced by an iodonitro-oxybenzene and the condensation product then converted in known manner into the final product. This subject-matter does not appear in the Specification as accepted. o-Iodohydroguinone monomethylether is prepared from o-iodo-p-amino-anisol by replacement of the amino group by the hydroxyl group. 3 : 4 : 5-Triiodo-1-benzonitrile is obtained by diazotizing 3:4: 5-triiodo-aniline and substituting the cyano group for the diazo group in known manner.