CH311607A - Process for the production of a new basic substituted fatty acid (2-halogen-6-methyl-anilide). - Google Patents

Description

  

  



  Process for the production of a new basic substituted fatty acid (2-halogen-6-methyl-anilide).



   The subject of the present patent forms a process for the production of a new basic substituted FettsÏure- (2-halo-6-methyl-anilids), which is characterized by the fact that a compound of the formula
EMI1.1
 in which X is a reactive, during the reaction a. The splitting radical means reacted with N-benzyl-N-n-butyl-amine.



   The radical X can be in a halogen atom or any other reactive substituent suitable for replacement with the basic radical, such as e.g. B. an alkylsulfonyloxy or arylsulfonyloxy group exist. The exchange of group X against the benzyl-butyl-amine residue takes place z. B. by simply heating with N-benzyl-N-bllt-yl-amine optionally in the presence of a basic re acting condensing agent or N-benzyl-N-butyl-amine in excess. The N benzyl-N-butyl-aminoaeet- (2-chloro-6-methyl-anilide) is a colorless oil, boiling below 0.1 mm Hg at 180¯, which after a while solidifies to colorless crystals which melt at 33. The base hydrochloride melts at 182-184¯.



   The new anilide is said to be used as a local anesthetic and as an intermediate for the production of other derivatives.



   Example:
100 parts by weight of chloroacet- (2-chloro-6-methyl-anilide) (obtained by reacting 2-chloro-6-methyl-aniline with chloroacetyl chloride in the presence of sodium acetate, melting point 140 to 141) are dissolved in 500 parts by weight of benzene suspended and treated with 157 parts by weight of N benzyl-N-butyl-amine. The temperature rises, and a large part of the reaction mixture goes into solution. The mixture is then stirred for 4 hours at room temperature and then for a few hours at boiling temperature. Then water is added, the mixture is made alkaline with sodium hydroxide solution and the oil which separates out is taken up in ether.

   After the ethereal solution has dried and the solvent has been driven off, an oil remains which is purified by vacuum distillation. 1t 7 parts by weight of pure N-benzyl-N-butyl-aminoacet- (2-chloro-6-methyl-anilide) are obtained, which corresponds to a yield e of 57%.



   PATENT CLAIM:
Process for the preparation of a new basic substituted fatty acid (2-halogen-6-methyl-anilide), characterized in that one is a compound of the formula

** WARNING ** End of DESC field could overlap beginning of CLMS **.



 

Claims (1)

** WARNING ** Beginning of CLMS field could overlap end of DESC **. Process for the production of a new basic substituted fatty acid (2-halogen-6-methyl-anilide). The subject of the present patent forms a process for the production of a new basic substituted FettsÏure- (2-halo-6-methyl-anilids), which is characterized by the fact that a compound of the formula EMI1.1 in which X is a reactive, during the reaction a. The cleaving radical means reacted with N-benzyl-N-n-butyl-amine. The radical X can be in a halogen atom or any other reactive substituent suitable for replacement with the basic radical, such as e.g. B. an alkylsulfonyloxy or arylsulfonyloxy group exist. The exchange of group X against the benzyl-butyl-amine residue takes place z. B. by simply heating with N-benzyl-N-bllt-yl-amine optionally in the presence of a basic re acting condensing agent or N-benzyl-N-butyl-amine in excess. The N benzyl-N-butyl-aminoaeet- (2-chloro-6-methyl-anilide) is a colorless oil, boiling below 0.1 mm Hg at 180¯, which after a while solidifies to colorless crystals which melt at 33. The base hydrochloride melts at 182-184¯. The new anilide is said to be used as a local anesthetic and as an intermediate for the production of other derivatives. Example: 100 parts by weight of chloroacet- (2-chloro-6-methyl-anilide) (obtained by reacting 2-chloro-6-methyl-aniline with chloroacetyl chloride in the presence of sodium acetate, melting point 140 to 141) are dissolved in 500 parts by weight of benzene suspended and treated with 157 parts by weight of N benzyl-N-butyl-amine. The temperature rises and a large part of the reaction mixture goes into solution. The mixture is then stirred for 4 hours at room temperature and then for a few hours at boiling temperature. Then water is added, the mixture is made alkaline with sodium hydroxide solution and the oil which separates out is taken up in ether. After the ethereal solution has dried and the solvent has been driven off, an oil remains which is purified by vacuum distillation. 1t 7 parts by weight of pure N-benzyl-N-butyl-aminoacet- (2-chloro-6-methyl-anilide) are obtained, which corresponds to a yield e of 57%. PATENT CLAIM: Process for the preparation of a new basic substituted fatty acid (2-halogen-6-methyl-anilide), characterized in that one is a compound of the formula EMI2.1 in which X is a reactive residue that is split off during the reaction, reacts with N-benzyl-N-butyl-amine. The N-benzyl-N-butyl-amino-acet- (2-chloro-6-methyl-anilide) obtained in this way forms a colorless oil boiling below 0.1 mm Hg at 180, which after some time becomes colorless, solidified at 33 "melting crystals. The hydrochloride of the base melts at 182-184¯. The new anilide will be used as a local anesthetic and as an intermediate product. SUBClaim: Process according to patent claim, characterized in that a halogenate (2-chloro-6-methyl-anilide) is allowed to react with N-benzyl-N-butylamine.