CH304946A - Process for the production of a condensation product. - Google Patents

Description

  

  



  Process for the production of a condensation product.
The present patent relates to a process for the production of a condensation product of the formula
EMI1.1
 characterized in that 4-chloro-5-trifluoromethyl-aniline is allowed to react with a halogenated carbonic acid derivative and the reactive carbamic acid derivative obtained is reacted with 2-amino-4,4'-dichloro-1,1'-diphenylthioether-6'sulphonic acid sodium.



   One embodiment of the process according to the invention consists in that 4-chloro-5-trifluoromethyl-a. Niline can react with phosgene and the 4-chloro-5-trifluoromethyl-phenyl-carbamic acid chloride obtained is reacted with 2-amino-4, 4'-dichloro-1, 1'-diphenylthioether-6'-sulfonic acid sodium. It is preferable to work in the presence of a tertiary base as the condensing agent. Pyridine or quinoline are particularly suitable for this purpose.



   Furthermore, 4-chloro-5-trifluoromethyl-aniline can be reacted with phosgene at an elevated temperature and the 4-chloro obtained is 5-f. rifluoromethyl-phenyl-isocyana. t with 2-a. bring mino- 4, 4'-diehlor-l, l'-diphenylthioether-6'-sulfonic acid sodium to the reaction, the compound of the above formula being obtained in good yield and excellent purity. A suitable solvent for this type of reaction is before a. III acetonitrile.



   Finally, one embodiment consists in that ma. N 4-chloro-5-trifluoromethyl-aniline can react with a halocarbonic acid ester and the 4-chloro-5-trifluoromethyl-phenyl-earbamic acid ester obtained with 2-amino 4, # -dichloro- l, l'-diphenylthioä. ther-6'-sulfonic acid reacts sodium.



   Mainly lower alkyl or aryl esters are suitable as halocarbonic acid esters. The conversion can advantageously be carried out in water.



   The new condensation product forms a pale crystal powder that is clearly soluble in hot water and can be used as a moth repellent.



     Example 1: a) 300 parts of dry benzene are saturated with phosgene at 70; to this end, a solution of 100 parts of 4-chloro-5-trifluoromethylaniline in 300 parts of dry benzene at 65-70 is added dropwise with stirring and introduction of phosgene. After some time, the mixture is heated to reflux and phosgene is introduced until only small amounts of the amine used are undissolved. The benzene solution is then filtered, the benzene is distilled off and the 4-chloro-5-trifluoro methyl-phenyl-isocyanate is fractionated.



     Kpa4: 92; Yield: 81 / o. b) 12.4 parts of 2-amino-4,4'-dichloro-1,1'-diphenylthioether-6'-sulfonic acid sodium are dissolved in 60 parts of acetonitrile with 7.38 parts of 4-chloro-5-trifluoromethyl-phenyl isoeyanate is added and warmed on a water bath for ten hours. The reaction solution is filtered and the solvent is evaporated.



  Yield: 15 parts.



   The condensation product is dissolved in 3000 parts of 80-85 water, mixed with a little animal charcoal and filtered hot. N / A. Before the addition of 140 parts of saturated sodium chloride solution, the condensation product separates out.



   After cooling, it is collected and dried in vacuo. In order to rid it of table salt, it can be extracted from absolute alcohol. After drying and grinding, the new condensation product forms a light-colored powder that is easily soluble in hot water.



   Example 2:
The 4-chloro-5-trifluoromethyl-phenyl-carbamic acid chloride prepared from phosgene and 4-chloro-5-trifluoromethyl-aniline in a dry, inert solvent gives, with the addition of pyridine as a condensing agent with 2-a-mino-4, 4'-dichloro-1, 1'-diphenylthioether-6'-sulfonic acid sodium, the urea described in Example lb) in a satisfactory yield.



   Example 3:
The one from chlorocarbonic acid phenyl ester and 4-chloro-5-trifluoromet. Hylaniline prepared in dry pyridine 4-chloro-5-trifluoromethyl phenyl-carbamic acid phenyl ester gives by reaction with 2-amino-4, 4'-dichloro-1, 1'-diphenylthioether-6'-sulfonic acid sodium in hot water the urea described in Example lb); instead of 4-chloro-5-trifluoromethyl-phenyl-ca. Phenyl amino acid esters can also be used in the corresponding methyl ester.

 

Claims (1)

PATENT CLAIM: Process for the preparation of a condensation product of the formula EMI2.1 denoted by the fact that 4-chloro-5-trifluoromethyl-aniline is allowed to react with a halogenated carbonic acid derivative and the reactive carbamic acid derivative obtained is reacted with 2- a. mino-4, 4'-diehlor-1, l'-diphenylthioether-6'ffulfonsa. urem sodium converts. The new condensation product forms a beautiful, light color that is clear in hot water. r soluble crystal powder that can be used as a moth repellent. SUBClaims: l .. Process according to claim, characterized in that 4-chloro-5-trifluoromethyl-aniline is allowed to react with phosgene and the 4-chloro-5-trifluoromethyl phenyl-carbamic acid chloride obtained is reacted with 2-amino-4,4 'dichloro-1, l'-diphenylt-hioether 6'-stilfonsaurem sodium converts. 2. The method according to claim, characterized in that 4-chloro-5-trifluoromethyl-aniline is allowed to react with phosgene at elevated temperature and the 4-chloro-5-trifluoromethyl-phenyl isocyanate obtained with 2-amino-4, 4'-diehlor-1, 1'-diphenylthioether-6'-sulfonic acid sodium converts. 3. The method according to claim, characterized in that 4-chloro-5-trifluoromethyl-aniline is allowed to react with a halocarbonic acid ester and the 4-chloro-5-trifluoromethyl-phenyl-carbamic acid ester obtained is reacted with 2-amino-4,4'- dichloro-1,1'-diphenyl thioether-6'sulphonic acid sodium converts.