SU509589A1 - The method of producing hydrochloride 2- (2,6-dichlorophenylamino) -imidazoline - Google Patents

Description

(54) METHOD FOR PRODUCING HYDROCHLORIDE 2- (2,6- DICHLOROPHENYLAMINO) 41Mi) 1AZOLINE

This invention relates to a new process for the preparation of 2- (2,6-dichlorophenylamino) -imidazoline hydrochloride (catapressan) of the general formula

: processability and high toxicity of CAC intermediate products and p & stock products. In most cases, as a semi-50, it consists in the fact that halides of aqueous phenylguanidine are of the general formula -ta-c-znz where Rf, 3 are halogen and / or il; The hydrogen atom or salt of this compound is reacted with an excess of ethylene diamine in an organic solvent at 100-2000G. The disadvantage of this method is the low yield of the target product (26-33%). Moreover, it is difficult to remove organic by-products by a known method. In order to simplify the process technology and increase the yield of the target product according to the proposed method, tetraalkylthiuramdisul-. the feed of the general formula (where R is methyl or ethyl, is chlorinated in an organic solvent, for example dichloroethane, obtained / V, jV-dialkyldichloromethyl ammonium chloride of the general formula L, R. where R has the above-mentioned values, is reacted with 2,6-dichloroaniline in the presence of a base, such as triethylamine, ' n best, N / V-dialkyl- / V (2,6-dichlorophenyl) -a-chloroformamidine of the general formula where I. has the above values, is treated with hydrogen chloride and the resulting hydrochloride is a compound of the total formula 1U is exposed to ethylenediamine solvent, for example, ethylene glycol. Example 1. Gilro.Chl () |) 1.1 .V, V,; U VUtil-L- (2, () - dichlorf.1t.1) - a-chloropho |) M11.ilia (from tetramethylthiuram. sulphyl ;.). A solution of 144 g (0.6 moltotrimetkltnuramdisulfide (thiuram) f-2.2 L liter of dry tho dichloroethane is saturated with chlorine (HOO g C /. In a process; chlorination of thiuram pollergic temperature 3f) cooling the reaction mass with a cold wave. At the end saturation of pa (; gently evaporated in vacuum (80-100 mm Hg. Art.) with IG) -4G1. To the residue, add 500 ml of aural dichloroethane and again distilled to 1:; ear in the same conditions. This operation is repeated 1000 ml of dry dichloroethane are added to the residue, and then, when changing and cooling (), a solution of 127 g of 2,6-dichl is gradually added Sraiilina and 238.6 g of triethylamine in 100 MJi of dry dichloroethane. Upon completion of the addition of 2,6-dichloroaniline and triethyl, the mixture is heated to 20-23 ° C and stirred at this temperature for 2.5 hours. The precipitated triethylamine hydrochloride is filtered and washed with dry dichloroethane. The combined filtrate is evaporated to dryness under vacuum (BO-100 mmHg), the residue is dissolved in 400 ml of acetone and to lacTBOpy according to (; alcohol bleach with carbon dioxide is added to complete the precipitation of hydrochloride L, L -dimethyl-L (2,6-dichlorophenyl) -a-chloroformamidine. The mixture is cooled in ice (1, G) -2 h), filtered and the precipitate is washed with acetone (3 × 50 ml). 183.58 g (94.2% of theory) of N, N-dimethyl- (2.8-dichlorophenyl). A-chloroformamidine hydrochloride are obtained, i.e. nj |. 14 () (with different). Found %: C37.65 and 3.32 C1 49.64 N 9.51. SdIySg h. Calculated,%: C 37.50; And 3.47; CMS, -30; N 9.72. Prim c p 2. Hydrochloride L, L-di-lil. V- (2,6-dichlorophenyl) -a-chloroformamilin (from tetraethylthiuram disulfide). This compound is prepared under the conditions of Example 1 from tetraethylthiuramdisulfyl. Melting WTypci melting the resulting product 73754:. Paydono,%; (41.95; And 4.51; C1 45.39; / V 8.77. Rijil, 4C - /, V ,.