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filingDate 1942-09-16-04:00^^<http://www.w3.org/2001/XMLSchema#date>
publicationDate 1944-08-23-04:00^^<http://www.w3.org/2001/XMLSchema#date>
publicationNumber GB-563621-A
titleOfInvention Improvements in preparation of compounds possessing the guanidine residue
abstract Sulphonamide compounds possessing the guanidine residue directly attached to an aromatic ring system are prepared by the action of a cyanogen halide on an aromatic sulphonamide containing a free amino group. The reaction may be carried out with or without an inert solvent such as dioxane, and the aromatic nucleus may be either unsubstituted or may carry a substituent such as an alkyl group. In examples: (1) p-Aminobenzenesulphonamide and cyanogen bromide are heated in a pressure vessel at 95 DEG C., the products extracted with water and then treated with alkali and then with acid to give diphenylguanidine-4 : 41-disulphonamide. (2) As in example 1 except that the reaction is carried out in dioxane solution. (3) p - Aminobenzenesulphonylguanidine and cyanogen bromide are reacted and worked up as in example 1 to give diphenylguanidine-4 : 41-disulphonylguanidine. Samples have been furnished under Sect. 2 (5) the preparation of which is as follows: (A) Cyanogen chloride and sulphanilamide are reacted and worked up under similar conditions to example 1 to give the same product. (B) As in example 3. (C) p-Aminobenzenesulphonanilide is reacted with cyanogen bromide in a pressure bottle to form diphenylguanidine-4 : 41-disulphonanilide. (D) 4 - Methyl - 3 - amino - benzenesulphonamide is reacted with cyanogen bromide in dioxane solution to form di-o-tolylguanidine-5 : 51-disulphonamide. (E) 2-(p-Aminobenzene-sulphonamido) pyridine is reacted with cyanogen bromide in a pressure bottle to form diphenylguanidine-4 : 41-disulphonamidopyridine. (F) 2-(p-Aminobenzenesulphonamido)-thiazole is reacted with cyanogen bromide in a pressure bottle to give diphenylguanidine-4 : 41-disulphonamidothiazole.
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