DD279669A1 - PROCESS FOR PREPARING 1-ARYL-3,5-BIS (ARYLAMINO) -4-HALOGEN-3-PYRROLIN-2-ONEN - Google Patents

Abstract

The invention relates to a process for the preparation of 1-aryl-3,5-bis (arylamino) -4-halo-3-pyrrolin-2-ones. Such compounds are useful as antibiotics. According to the object of the invention to provide a technically simple and economic method for the synthesis of these compounds based on readily available starting materials, Mucohalogensaeurederivate invention of general formula II with primary arylamines of general formula III in non-polar solvents in the temperature range of 10 to 50C reacted. Formulas II and III

Description

in the

X has the abovementioned meaning and Z is an alkyloxy, aryloxy, halogen, carbamoyl-alkylcarbonyloxy or arylcarbonyl group

means, with primary amines of the general formula III,

in the

R ¹ and R ^{2 have} the abovementioned meanings, are reacted in a non-polar solvent at temperatures in the range between -10 and 50 ° C.

2. The method according to claim 1, characterized in that is used as unpoiares solvent chloroform, dioxane or benzene.

3. The method according to claim 1 and 2, characterized in that is reacted at temperatures between and 30 ⁰ C.

Field of application of the invention

The invention relates to a process for the preparation of 1-aryl-3,5-bis (arylamino) -4-halo-3-pyrrolin-2-ones, which are suitable as antibiotics.

Characteristic of the known state of the art

So far, no method for the preparation of 1-aryl-3,5-bis (arylamino) -4-halo-3-pyrrolin-2-ones known.

Object of the invention

The object of the invention is to develop a technically simple and economical method for the preparation of 1-aryl-3,5-bis (arylamino) -4-halo-3-pyrrolin-2-ones using readily available starting materials.

Explanation of the essence of the invention

The object of the invention is to produce 1-aryl-3,5-bis (ar / lamino) -4-halo-3-pyrrolin-2-one using readily available starting materials.

This object is achieved by a process for the preparation of 1-aryl-3,5-bis (arylamino) -4-halogeno-3-pyrrolin-2-ones of the general formula I,

in the

X is halogen, preferably chlorine or bromine, and

R 'and R ^{2 are} hydrogen, halogen or alkyl and Alkyloxygi uppen with up to 5 carbon atoms by erfindungsyemäß Mucohalogensäurederivate the general formula II,

O ^

in the

X has the abovementioned meaning and

Z is an alkyloxy, aryloxy, halogeno, carbamoyl-.AIkylcarbonyloxy- or Arylcarbonylcxygruppe, with primary amines of general formula III,

in the

R 'and H ^{1 have} the abovementioned meanings, in nonpolar solvents, preferably chloroform, dioxane and benzene, at temperatures in the range between -10 and 50 ° C, preferably between 10 and 30 ⁰ C, are reacted.

The final product is obtained by adding water or filtration and then removing the solvent in vacuo.

The Muclohalogensäurederivate of the general formula II used as the starting stage for the process according to the invention are easily accessible by known technical methods.

embodiments example 1

0.5 g (2.67 mmol) of mucochloric acid pseudochloride are dissolved in 5 ml of chloroform. Is added dropwise within 10 minutes while stirring at 20 ^c C 1.14g (13,3mmol) of aniline, dissolved in 10 ml of chloroform to. The mixture is stirred for 24 h at 2O ⁰ C, filtered, washed with dilute hydrochloric acid and water and dried over MgSO ₄ . After evaporation in vacuo (Th d 80%..) Are obtained 0.8 g of 1-phenyl-3,5-bis (phenylamino) -4-chloro-3-pyrroline-2-one of melting point 176 to 178 ⁰ C.

Example 2

In the reaction of 1, Og (5.46 mmol) mucochloric acid pseudomethyl ester with 2.03 g (21.84 mmol) of aniline analogously to Example 1, 1.7 g (83% of theory) of 1-phenyl-3,5-bis (phenylamino ) -4-chloro-3-pyrroline-2-one of melting point 176 to 178 ⁰ C.

Example 3

The reaction of 0.5 g (2.67 mmol) mucochloric acid pseudo chloride with 1.42 g (13.3 mmol) p-toluidine analogously to Example 1 gives 0.47 g (43% of theory) of 1- (p-tolyl) -3,5- bis (p-tolylamino) -4-chloro-3-pyrrolin-2-one of melting point 173 to 175 ° C.

Example 4

The reaction of 0.5 g (2.67 mmol) mucochloric acid pseudo-chloride with 1.62 g (13.3 mmol) of p-anisidine analogously to Example 1 gives 0.54 g (43% of theory)! (P-methoxyphenyl-SB-bis-p methoxyphenylaminoM-chloro-S-pyrroline ^ -one of melting point 149 to 151 ° C.

Example 5

The reaction of 0.5 g (2.67 mmol) mucochloric acid pseudo-chloride with 1.14 g (13.3 mmol) aniline in benzene gives, as in Example 1, 0.48 g (48% of theory) of 1-phenyl-3,5-bis (phenylamino ) -4-chloro-3-pyrrolin-2-one of m.p. 176-178C.

Claims (1)

claims: 1. A process for the preparation of 1-aryl-3,5-bis (arylamino) -4-halogeno-3-pyrrolin-2-ones of the general formula I, in the X is halogen, preferably chlorine or bromine, and R ¹ and R ^{2 are} hydrogen, halogen or alkyl and alkoxy groups having up to 5 carbon atoms, characterized in that mucohaiogenic acid derivatives of the general formula II,