CH214901A - Process for the preparation of a halogen-containing acylaminosulfonic acid. - Google Patents

Description

  

  Process for the preparation of a halogen-containing acylaminosulfonic acid. It has been found that valuable halogen-substituted acylaminosulphonic acids of the aromatic series are obtained if amino sulphonic acids of the benzene series which contain replaceable hydrogen on the nitrogen atom are obtained with acids of the diphenyl ether or. Diphenyl sulfide series respectively. converts their reactive derivatives, the reaction components being selected in such a way that

   that at least one halogen atom is present in the end product.



  As acids of diphenyl ether respectively. The diphenyl sulfide series are the free carboxylic acids, but especially their reactive derivatives, such as the chlorides or esters; the corresponding sulfonic acid chlorides come into consideration in the same way.

   Nuclear halogenated and resp. or alkylated diphenyl ethers respectively. Diphenyl sulfide carboxylic or sulfonic acids. They can be easily represented using known methods.

   For example, starting from halogenated or alkylated aminodiphenyl ethers or diphenyl sulfides, the carboxylic acids can easily be obtained via the Ni triles. The corresponding sulfonic acids are obtained, for example, by oxidation of the sulfinic acids, which in turn can be prepared from diazotized aminodiphenyl ethers using sulfur dioxide.

    It is of course also possible to use the sulfonation products, sulfonic acids, such as their chlorides, which can be obtained directly from diphenyl ethers in the customary manner with sulfonating agents.



  Suitable aminosulfonic acids are, for example, o-anilic acid, 3,4-dichloroanilinesulfonic acid, 4-chloroaniline-2-sulfonic acid, benzidinedisulfonic acid, m-phenylenediaminesulfonic acid, etc. The compounds prepared in the manner indicated above are suitable for a wide variety of uses Purposes, but especially for use as a moth repellent.



  The subject of the present patent is a process for the preparation of a halogen-containing acylaminosulfonic acid, characterized in that 3,4-dichloroaniline-6-sulfone
EMI0001.0063
  
EMI0001.0064
  
EMI0001.0065
      acid is reacted with 4-chloro-1,1'-diphenylether-4'-carboxylic acid chloride.



  As a sodium salt, the new compound is an almost colorless powder that dissolves well in hot water and can make animal fibers real to moths. Example: 24 parts of 3,4-dichloroaniline-6-sulfonic acid are suspended in 100 parts by volume of pyridine, at 20 with 30 parts of 4-chloro-1,1 '- diphenyl ether - 4' - carboxylic acid chloride,

         185 '(. Shown in the customary manner from 4-chloro-1,1'-diphenyl ether-4'-carboxylic acid and phosphorus pentaelloride) and stirred for 10 hours at ordinary temperature. Then it is distilled with steam, mixed with bicarbonate solution, taken up in plenty of hot water and filtered. The condensation product is precipitated in crystalline form from the hot filtrate with brine. It is suctioned off, washed with cold water and net getrock in vacuo.

   It has the following constitution:
EMI0002.0021
    As the sodium salt, the new compound is an almost colorless powder that dissolves well in hot water and can make animal fibers real to moths.



  The 4-chloro-1,1'-diphenyl ether @ -4'-carboxylic acid, F. <B> 168 ', </B> is obtained by saponifying the 4 - chlorine - 4' - cyano - 1,1 '- dipherrylätlrers, Kp. o, i; ni, ', 160, F. 81 to 83, obtained by means of boiling 20% aqueous sodium hydroxide solution. The cyano compound can be made from diazotized 4-chloro-4'-amino-1,1'-diphenyl ether according to known processes.

 

Claims (1)

PATEN TANSPRZTCH Process for the preparation of a halogen-containing acylaminosulforric acid, characterized in that 3,4-dichloroaniline-6-sulforric acid is reacted with 4-chloro-1,1'-diphenyl ether-4'-carbo-nyl chloride . As sodium salt, the new compound is an almost colorless powder which is readily soluble in hot water and which can make animal fibers moth-proof.