DE865143C - Process for the preparation of benzene sulfonamides of the dioxalane series - Google Patents

Description

Process for the preparation of benzene sulfonamides of the dioxalane series The subject of patent 858 565 is a process for the preparation of sulfonamides the z, 3-dioxane series, in which one i, 3-dioxanes, the primary or secondary amino groups contain, with sulfonic acid halides of the benzene series, which have an amino group or contain a group convertible into an amino group.

It has now been found that in place of the amino compounds i, 3-Dioxaureihe also those of the dioxalane series, the z ring carbon atom less contain as i, 3 = dioxanes, can be used as starting materials for this reaction. Amines of the dioxalane series are z. B. by reacting monochlorodioxalanes with ammonia or primary amines. The monochlorodioxalanes in turn are for example obtainable by chlorinating dioxalanes or by reacting chlorine-z, a-diols with formaldehyde or other carbonyl compounds in the presence of acids at increased Temperature.

The implementation of aminodioxalanes with sulfonic acid halides takes place in the manner customary for these reactions, if appropriate in the presence of a solvent and an acid-binding agent. the obtained dioxalanesulforiamide are, if necessary after conversion of the convertible into an amino group Group in the benzene residue into an amino group, in particular also in the form of the acylamino compound, usable as a remedy. For example, they stand out from the usual sulfonamides in the treatment of wounds by the fact that besides bactericidal they also have a have hemostatic effects.

The parts given in the example below are parts by weight. Example A solution of 2o6 parts of 4-methylaminodioxalane in 40o parts of methanol is under vigorous stirring at 25 ° gradually with 466 parts of N-acetylsulfanilic acid chloride offset. You can then slowly .concentrated aqueous sodium carbonate solution to to flow in to the alkaline reaction, sucks in the separated crystal pulp cooling and crystallizes from hot water with the addition of some animal charcoal around. 36o parts of 4-N-acetylaminobenzene-z-sulfonic acid amide of 4-aminomethyldioxalane are obtained in this way with a melting point of z38 °.

To deacetylate 54o parts of the acetyl compound with 300 Parts of concentrated hydrochloric acid in 40oo parts of methanol are brought to the boil for 2 hours Heated to reflux. After cooling, the solution becomes more methyl alcoholic Potassium hydroxide neutralized, the precipitated potassium chloride sucked off and cie solution evaporated. The remaining solid residue is made from hot water with the addition recrystallized from some animal charcoal. 35o parts of 4-aminobenzene-z-sulfonic acid amide are obtained of 4-aminomethyldioxalane (F. = = og °).

4-Chloromethyldioxalane is treated to produce 4-methylaminodioxalane (made from 3-chloropropanediol-x, 2 and formaldehyde) in an aqueous medium with Ammonia in the pressure vessel at zoo °. After the excess ammonia has evaporated the solution is made strongly alkaline and the 4-methylaminodioxalane by distillation won (bp = 165 to r70 °).

Claims (1)

PATENT CLAIM: Process for the production of benzenesulfonamides of Dioxalane series in a further development of the patent 858 565, characterized in that one dioxalanes containing primary or secondary amino groups with sulfonic acid halides the benzene series converts which has an amino group or one which can be converted into an amino group Group included.