The method of obtaining n,n-di(cyclohexyl)amide sorbic acid

 

(57) Abstract:

The inventive product is N, N-di(cyclohexyl)amide sorbic acid. T. pl. = 75 - 79oC (with decomp.). Reagent 1: N,N-di(cyclohexyl)-amine. Reagent 2: a solution of acid chloride of sorbic acid, obtained by the interaction equimolar amounts of sorbic acid and Teilhard in the medium of organic solvent in an acid environment. Reaction conditions: in the midst of the same solvent selected from the group: heptane, hexane, benzene, at a molar ratio of acid chloride of sorbic acid and N,N-di(cyclohexyl)amine of 1 : 2,2, with the gradual addition of the amine.

The invention relates to the chemistry of obtaining amides sorbic acid (TRANS, TRANS-2,4-hexadienoic acid), in particular the production of N,N-di(cyclohexyl)amide sorbic acid of the formula (N GOS. registration 506976).

CH3SN=SSN=N(cyclo-C6H11)2(I)

Further, this amide is called as dicomed. To date, synthesized a large number of sorbic acid amides (I, s 53 FF. ); some of them are widely used in medical practice (as analeptics, local anesthetics, analgesics, germicidal drugs) and amides sorbic acid is carried out in accordance with the technology, widely used in organic chemistry, namely by reacting the acid chloride sorbic acid (hereinafter referred to as has) with the appropriate amine. So, for example, stated [2] use as herbicides and plant growth regulators amides 2,4-hexadienoic acid formula

AG-Y-CH(R)CH=SSN=N(R1)2(II) where R=the atom H or a group CH3Y=an atom or a divalent atom S; R1=atom H, C1-C4-alkyl, C2-C4alkenyl,2-C4-quinil, cyclo-C3-C6-alkyl, phenyl, benzyl; AG=(UN)substituted phenyl, peredelnyj, nattily, quinoline radical or phenoxy-phenyl or pyridyloxy-phenyl group.

Amides of the formula (II), as well as ethers or tilapia receive [2] from the esters of 2,4-hexadienoic acids (mainly from the methyl ester) of the formula (III)

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Moreover, the known method [2] to obtain the esters of the formula (III), whereas in respect of the receipt of the acids of formula (IV), the acid chloride of the formula (V), esters of the formula (VI), tilapia formula (VII) and amides of formula (II) use classical methods, widely used in organic chemistry, the esters of the formula (III) can be converted by hydrolysis into the carboxylic acid by papertape, thiols or amines with the formation respectively of the esters of formula (VI), tilapia formula (VII) or amides of formula (II), including N,N-di(cyclohexyl)amide 5-aryloxy - or 5-aaltio-substituted 2,4-hexadienoic acid of formula (II), where R1cyclo-C6-alkyl (prototype).

The most common classical method of obtaining amides 2,4-hexadienoic acid and its substituted analogues is the interaction of carboxylic acids, for example has, with the amine (I, s 53 FF.). In turn has can be obtained by a commonly known method using various halogenation agents such as Sl2, l3, l5or other (I, s 49 FF.). When the molar ratio of reagents acid halogenation agent:1 or more, ask:amine=1:2 or more second amine molecule is an acceptor Hcl produced in the reaction:

RCOCl+2NHR12___ (RCO-NR12+HCl) RCO-NR12+RCONHR12- C - C--N

C 166,75 (s-1), 121,67 (C-2), 141,55 (C-3), 130,74 (C-4), 136,26 (C-5), 18,60 (C-6); ring: 56,62 (s-1 ), 31,35 (C-26 ), 26,5 (C-35 ), 25,58 C-4 ); molecular weight: found 275, calculated 275,44.

P R I m e R 1. Obtaining N,N-di(cyclohexyl)amide sorbic acid in the environment of heptane.

Getting chloranhydride, thermometer, stirrer, water cooling and heating load of 33.6 g (0.3 mol) of sorbic acid and 700 ml of heptane. In the resulting suspension with constant stirring from the dropping funnel was added dropwise 35,75 g (0.3 mol) of thionyl chloride; the molar ratio of reactants is 1:1. The temperature should not rise more than 50aboutC. After loading the calculated quantity of chloride tiomila the temperature in the flask was raised to the boiling point of the solvent and give exposure at this temperature and stirring for 5-6 hours after exposure of the reaction mass is cooled to 18-28aboutC and filtered from unreacted acid. The filtrate is a solution of the acid chloride of sorbic acid in the solvent (heptane) is sent to the next stage.

Obtaining N,N-di(cyclohexyl)amide sorbic acid (dynamid).

In the flask is charged with the above solution of acid chloride of sorbic acid in heptane. Then under stirring was added dropwise 119,66 g (0.66 g-mol) of N, N-di(cyclohexyl)amine (DCGA). The molar ratio hack:DCHA is 1: 2,2. The addition of DCGA carried out slowly at a temperature in the reaction mass not exceeding 30aboutC. After loading the estimated number of DCGA the temperature in the reaction maschine this time, the reaction mass solution dazamide in the solvent, as well as unreacted excess amine source, the remains of the hydrochloride of DCHA, salts of sulfur compounds is cooled to 18-20aboutWith and sucked hydrochloride source Amin DCHA. Hydrochloride, DCHA on the filter is washed 2-3 times with a solvent and sent for regeneration. Wash the filtrate is added to the main filtrate and then all together sequentially washed with water and 5% hydrochloric acid to pH 3-4. Fell in the latter case, the hydrochloride of DCGA filtered off and send it to regeneration. The filtrate is transferred into a separating funnel and separated layers: the acidic aqueous layer is neutralized and the organic layer washed with water until neutral and the solvent is distilled off under reduced pressure (100-300 mm RT.cent.), making sure that the temperature in the reaction mass does not exceed 45-50aboutC. the distillation Process stop after selection of not less than 2/3 part of the solvent from the initially loaded into the reaction. Then the VAT residue is transferred into a crystallizer equipped with a thermometer and stirrer, and gradually cooled to 5-7aboutWith, ensuring that no heat crystallising mass. Fallen in this white crystallising the product hoteltravel is Yes, what is 48-52% of theory, counting on from the reaction of sorbic acid. From the filtrate after separation of the main quantity of the crystals dinamica further condition on the cold additionally allocated 4,2-5,1 g or 5.1% and 6.2% of the target product. Thus the total yield of the target diamide is 54,2-7,1%

The content of the main product is 98,7-and 99.8% (GC). Tpl.=75-79aboutC (decomp.).

P R I m m e R 2. Obtaining N,N-di(cyclohexyl)amide sorbic acid in the environment of hexane.

Instrumentation process, the number of downloads of the reaction and solvent, synthesis, isolation and purification of the target product are the same as in example 1. The difference is that as hexane solvent used instead of heptane.

Get a 32.6 g (38.7 per cent ) crystal diamide and then upon further standing in the cold for 2 days obtained 13 g (15.7 per cent). The thus obtained 45.6 g dazamide, representing 54.4% of theory, counting on from the reaction of sorbic acid; the content of the basic substance is 99,8% Tpl.=76-78aboutC (decomp.).

P R I m e R 3. Obtaining N,N-di(cyclohexyl)amide sorbic acid in the environment of benzene.

Instruments the cleaning product is the same, as in example 1. The difference is that as benzene solvent used instead of heptane.

Get 24 g (29%) of crystalline diamide and then upon further standing in the cold for 5-7 days to received 20 g (24.2 per cent). The thus obtained 44 g of the target dinamica that is 53.2% of theory, counting on from the reaction of sorbic acid; the content of the basic substance is 98.3-99,63% Tpl.=75-79aboutC (decomp.).

The METHOD of OBTAINING N,N-DI(CYCLOHEXYL)AMIDE SORBIC ACID, characterized in that N, N-di(cyclohexyl)amine is subjected to interaction with the solution of acid chloride of sorbic acid, obtained by the interaction of equimolar amounts of sorbic acid and thionyl chloride in the medium of organic solvent in an acid environment, and the process is conducted in an environment of the same organic solvent selected from the group: heptane, hexane, benzene, at a molar ratio of acid chloride of sorbic acid and N, N-di(cyclohexyl)amine of 1 : 2.2 for the gradual addition of the amine.

 

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