DE733514C - Process for the preparation of aromatic sulfonic acid amides - Google Patents

Description

GERMAN EMPIRE

ISSUE MARCH 29, 1943

REICH PATENT OFFICE

PATENT LETTERING

CLASS 12 q GROUP 22 oi

I 64685 IVc / 12 q

Dr. Hans Krzikalla and Dr. Oskar Ferrares in Ludwigshafen, Rhine,

have been named as inventors.

I. G. Farbenindustrie AG. in Frankfurt, Main Process for the production of aromatic sulfonic acid amides

Patented in the German Reich from May 26, 1939 Patent issued February 25, 1943

According to Section 2 (1) of the ordinance of July 20, 1940, the declaration has been made, that protection should extend to the Protectorate of Bohemia and Moravia.

It has been found that you can easily

Catfish aromatic sulfonic acid amides are obtained when alkyl or halogen substituted Arylene-o-sulfonylides (cyclic double esters of phenol-o-sulfonic acids) with ammonia or organic, basic derivatives of ammonia heated, the at least one contain free hydrogen atom on nitrogen. The implementation is, for example, after following equation

Cl

OO
SO

0 0

+ 2 NH ₃

Cl

-> 2

0-

OH

CH _n

0 0

CH,

The arylenosulfonylides used as starting materials can, in addition to alkyl groups or Halogen atoms also have other substituents, e.g. B. alkoxy or sulfonic acid groups contain. Halogen-containing sulfonylides, such as those used, for example, are particularly easy to implement according to the procedure of patent 711710 receives. The sulfonylides can also contain substituents that interfere with ammonia or its organic descendants

738514

realize; one then chooses the amount of base appropriately large.

= _ ■ - ".-. Basic organic derivatives of ammonia, which can be used for the reaction are those which are capable of forming acid amides, e.g. B. primary and secondary aliphatic, hydroaromatic, cycloaliphatic or aromatic amines, or heterocyclic basic nitrogen compounds with NH groups, such as piperidine, Pyrrolidine, tetrahydroquinoline or dihydroindole.

The reaction can take place in the presence of a solvent which does not interfere with the reaction be effected, e.g. B. in aromatic hydrocarbons or in dichlorobenzene or in water, if you ensure that the saponification of the amide is prevented. The reaction temperature is generally between Sun and i6o °. If necessary, one works under increased pressure, for example if you use ammonia or gaseous basic compounds at elevated temperature want to implement.

The compounds prepared according to the invention can be used as intermediates, for example in the manufacture of dyes and textile auxiliaries.

The parts given in the examples below are parts by weight unless they are otherwise noted.

Example i ⁼

45 parts of 2, 4-dichlorophenylene-o-sulfonylid (prepared from 4, 6-dichlorophenol and chlorosulfonic acid according to the patent 711 710) are heated with 200 parts of sodium I7 ° / _o aqueous ammonia for 5 hours at 145 ⁰ in a stirred autoclave. On acidification of the reaction mixture with hydrochloric acid gives the 2, 4-dichlorophenol-6-sulfonic acid amide, which tallisiert of o-dichlorobenzene umkris _s, melts at 230 ^0th

In a corresponding manner, with excess pyrrolidine, 2,4-dichlorophenol-δ-sulfonic acid pyrrolidide (F. = 146 ^° ) is obtained, with excess aniline, 2,4-dichlorophenol-6-sulfonic acid anilide (F. = 87 ^° ).

Heating 2,4-dichlorophenol-o-sulfonylid with n-butylamine in benzene for 6 hours at the boil under reflux, we obtain 2, 4-dichlorophenol-6-sulfonic acid n-butylamide (mp = 88 °); Dibutylamine provides 2,4-dichlorophenol-6-sulfonic acid dibutylamide in a corresponding manner.

Leaves from palm kernel fatty amine or palm kernel fatty methylamine in boiling o-dichlorobenzene 2,4-dichlorophenol-6-sulfonic acid palm kernel fatty amide or palm kernel fatty methylamide produce.

Example 2

4-Chloro-2-methylphenylene-o-sulfonylide (prepared from 4-chloro-6-methylphenol and chlorosulfonic acid according to Patent 711,710) is heated with pyrrolidine in the manner described in Example 1. On acidification of the reaction mixture with hydrochloric acid yields the 4-chloro-2-methylphenol-6-sulfonsäurepyrrolidid, which, recrystallized from ligroin, melts at 126 ^0th

Example 3

53 parts of "2-methylphenylene-o-sulfonylid-4, 4'-disulfonic acid chloride (see Monthly Bulletins for Chemistry, Vol. 46, p. 388) are 100 parts Pyrrolidine heated to boiling for 2 hours. When the reaction mixture is acidified with hydrochloric acid, this is obtained .2-methylphenol-4,6-disulfonic acid pyrrolidide, which, recrystallized from gasoline, melts at 153 °.

Example 4

60 parts of cyclohexylamine are added to 90 parts of 2,4-dichlorophenylene-o-sulfonylide (see Example 1), a vigorous reaction immediately taking place, which is noticeable by an increase in temperature. Then is heated for 2 hours at about 120 ^0, crushes the brown in the form of lumps product obtained and washing it with very dilute hydrochloric acid. It is then dissolved in hot ethyl alcohol, the unchanged o-sulfonylide remaining as a residue. After filtering through animal charcoal, the filtrate is obtained after evaporation of the alcohol, the 2,4-DiChIOrPhCnOI-O-SuIfOnSaUrCCVcIohexylamid. It is a weakly colored resin that solidifies to almost colorless crystals after a short time.

Claims (1)

Claim: Process for the preparation of aromatic sulfonic acid amides, characterized in that that one alkyl or halogen substituted arylene-o-sulfonylides with Ammonia or organic basic derivatives of ammonia heated, no which contain at least one free hydrogen atom on the nitrogen. BEEUN. GEDWW IN DKR