SU944503A3 - Process for producing derivatives of benzimidazole or their tautomers - Google Patents

Description

The goal is achieved by the fact that the compound of the general formula 1) is IJ where R "-R., Y, t, x have the indicated values are reacted with carbon disulfide at 10-150 ° C, preferably at SOYO C, in water or in an organic solvent in the presence of a base with the release of the target product. As an organic solvent, for example, alcohols such as methyl, ethyl or propyl, hydrocarbons such as benzene or toluene, or chlorinated hydrocarbons, in particular chlorobenzene or methylene chloride, are used. By base is meant, for example, alkalis, tertiary amines or organic bases such as pyridine. Some of the starting compounds used to prepare the compounds of formula (I) of the invention are known substances. p g col / I Preparation of 5-chloro-6-G2, h-dichlor-h „,. , : .. ... phenoxy) -2H-1,3-dihydrobenzimidazolthion-2. 256.2 g of 4-chloro-5- (2, dichlorophenoxy) -1,2-phenylediamine are introduced into a solution of 135.6 g of potassium hydroxide in ml of absolute ethanol. Then, with stirring and at room temperature without cooling, 2 g of carbon disulfide is added dropwise to the mixture within half an hour. The reaction proceeds with a large exothermic effect. During the second quarter of an hour of addition of carbon disulfide a brown precipitate is formed. Immediately after that, the mixture is heated to reflux and boiled for 6 hours and maintained at a bath temperature of 60 ° C, after which the reaction mixture is stirred for 15 hours at room temperature. The suspension is poured into 6 l of ice-cooled water, the precipitate is filtered off, washed with approximately 3 l of water and dried in vacuo at. The crude product is dissolved in 10 liters of hot acetone, the solution is clarified with activated carbon, filtered through Hyflosuperui, the solution is evaporated to 4 liters and then cooled to 0 ° C. The precipitate is filtered off, washed with acetone and dried in vacuum at 40 ° C. As a result, 266 g of 5-chloro-6- (2,4-dichlorophenoxy) -2H-1, α-Dihydrobenzimidazolthion-2 are obtained at an oppo rage of 309-311 C. The yield of the product 91 is 91. Table. 1 ukazan compounds obtained similarly.

- ten

Continued table. one

lore

Chlorine CHjUOj - VoChlor2-chloro-methoxyphenoxy

2-chloro-methylphenoxy

Chlorine

| -metiparbonyl 2-chlorophen chlorine

hydroxy.

2, dichlorophenoxy

Bromine

/ 7 V

LHH.

WN

Chlorine 2-o1 si-hporfenoxy H 2,5-dichlorophenoxy

H2B-Dimethylphenoxy

H2-tert.-butylphenoxy

Methoxyphenoxy

Methoxyphenylthio

ETOXY 2,3-DEGREE | X |) € NOXI

Bootie - with

hydroxy2, -Aichlorfenoxy

BromSE

 , 0

SO t-SOfe

2Y-257

W

290

h 275-276

267-275

200-207 290-302

305-307. 257-259

250-253 255

Claims (1)

276-280 in the table. 2 shows compounds prepared similarly. Table 2 Temperature Compound melting tour, ° C e, -Q. H ci- / Vo S 350-355 C1. -OoOS 291-294 .-- :: - The obtained biologically active substances are used to combat worms that parasitize in such domestic and useful animals as cattle, sheep, Goats, cats and dogs. Biologically active substances can be administered to animals as a single dose or repeatedly, and depending on the type of animal, the dose administered at one time is preferably 0.5-100 mg per body weight. In some cases, a better effect can be achieved through longer administration, or: a smaller total dose can be dispensed with. Biologically active substances or mixtures containing these substances can also be mixed to feed or drinking water. In the prepared feed, the substances of formula (I) can be contained, mainly in a concentration of 0.005-0.1 weight. The agent can be prepared in the form of a solution, a suspension emulsion (Drenchs), powder of tablets, pills and capsules, which are introduced into animals through mouth or abomasal. For the preparation of the indicated preparations, for example, SS are the usual solid carrier substances, such as kaolin, talc, bentonite, cooked calcium phosphate, cotton seed flour, or such non-reactive liquids such as oils and others, solvents and diluents that are harmless to the body of the animal. If the physical and toxicological properties of the solution allow this, then biologically active substances can be introduced into animals, for example, subcutaneously. In addition, it is possible to introduce a biologically active substance in animals using feed salt in bars (salt) or blocks of molasses. If the agent is in the form of a feed concentrate, then the carrier material is, for example, hay, feed, feed grain or protein concentrate. In addition to the biologically active substance, such food may additionally contain other additives, vitamins, antibiotics, chemotherapeutic agents or other pesticides, mainly means that inhibit the infection of bacteria, suspend the growth of fungi, coccidiostatic agents or hormonal preparations, substances that have anabolic effects or substances growth-promoting, affecting the quality of the meat of animals, or beneficial to the body in other ways. The proposed biologically active substances can also be used in combination with other Lactohelminthic substances, as a result of which the spectrum of action of the agent can be extended, or its activity can be brought in accordance with the circumstances. Preparation of anthelmintic agent is carried out by known methods. The invention The method of producing benzimidazole derivatives of the general formula Vyjyi s. (I) 1R 1 where Rn and R. are independently of one another denote hydrogen, halogens or methyl radicals; R «is hydrogen, halogen, methyl radical or methoxyl residue; X is oxygen or sulfur; Y is halogen, an alkyl radical containing l-t carbon atoms, an alkoxy residue containing 1-4 carbon atoms, methylthio. The group, methylsulfinyl residue, methylsulfonyl residue, trifluoromethyl residue, nitro group, hydroxyl group, nitrile group or acetyl residue, m takes O, 1.2 or 3, or their tauromers, wherein the compound of the formula </ BR> where R 4 X X have the indicated values , is reacted with carbon disulfide at 10-150 0, preferably between 30-100; in water or in an organic solvent in the presence of a base to release the desired product. Sources of information taken into account in the examination 1. UK patent H 1344548, cl. With 2 with, publish, 1974.