SU293793A1 - METHOD FOR OBTAINING CHLORINE DIMETHYLPHENYL - {3-METHYLBUTEN-2-IL) AMMONIUM - Google Patents
METHOD FOR OBTAINING CHLORINE DIMETHYLPHENYL - {3-METHYLBUTEN-2-IL) AMMONIUMInfo
- Publication number
- SU293793A1 SU293793A1 SU1346547A SU1346547A SU293793A1 SU 293793 A1 SU293793 A1 SU 293793A1 SU 1346547 A SU1346547 A SU 1346547A SU 1346547 A SU1346547 A SU 1346547A SU 293793 A1 SU293793 A1 SU 293793A1
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- dimethylphenyl
- ammonium
- methylbuten
- obtaining chlorine
- ether
- Prior art date
Links
- -1 CHLORINE DIMETHYLPHENYL Chemical class 0.000 title description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 title 1
- 229910052801 chlorine Inorganic materials 0.000 title 1
- 239000000460 chlorine Substances 0.000 title 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 239000003814 drug Substances 0.000 description 3
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 3
- JLTDJTHDQAWBAV-UHFFFAOYSA-N Dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 2
- WEVYAHXRMPXWCK-UHFFFAOYSA-N acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 2
- 229940027983 antiseptics and disinfectants Quaternary ammonium compounds Drugs 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 229940079593 drugs Drugs 0.000 description 2
- 230000003993 interaction Effects 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- DCCQEPFMJMZBQH-UHFFFAOYSA-N 2-methylbuta-1,3-diene;hydrochloride Chemical compound Cl.CC(=C)C=C DCCQEPFMJMZBQH-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 229940075930 picrate Drugs 0.000 description 1
- OXNIZHLAWKMVMX-UHFFFAOYSA-M picrate anion Chemical compound [O-]C1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-M 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Description
Изобретение относитс к способу получени новых, не описанных в литературе четвертичных аммониевых соединений, которые обладают фармакологической активностью и могут найти применение в ветеринарии дл лечени животных.The invention relates to a method for producing novel quaternary ammonium compounds that are not described in the literature, which have pharmacological activity and can be used in veterinary medicine for the treatment of animals.
Известен способ получени четвертичных аммониевых соединений взаимодействием третичных аминов с галоидными алкилами (реакци Гофмана) при нагревании в присутствии органического растворител .A method of producing quaternary ammonium compounds by reacting tertiary amines with halide alkyls (Hoffman reaction) when heated in the presence of an organic solvent is known.
Предлагаетс способ получени четвертичного аммониевого соединени , а именно хлористого диметилфенил- (З-метилбутен-2-ил) аммони , заключающийс во взаимодействии диметиланилина с хлоргидратом изопрена в нормальных услови х с последующим выделением целевого продукта путем промывки реакционной массы эфиром и вакуум-сушки. Предлагаемый способ вл етс более простым по сравнению с известным, поскольку позвол ет проводить процесс в обычных услови х (нормальна температура) и при отсутствии растворител .A method is proposed for the preparation of a quaternary ammonium compound, namely dimethylphenyl- (3-methylbutene-2-yl) ammonium chloride, consisting in the interaction of dimethylaniline with isoprene hydrochloride under normal conditions, followed by separation of the target product by washing the reaction mass with ether and vacuum sushi. The proposed method is simpler than the known one, since it allows the process to be carried out under normal conditions (normal temperature) and in the absence of a solvent.
Пример 1. Хлористый диметилфенил- (3метилбутен-2-ил ) аммоний.Example 1. Chloride dimethylphenyl- (3methylbuten-2-yl) ammonium.
Смесь 12Гг (I лолб) дймётйланйлйна и 104,5 г 1-хлор-3-метилбутен-2 оставл ют сто ть при комнатной температуре в течение 5 дней. Опевшие кристаллы промывают 200 мл сухогоA mixture of 12 Gg (I lolb) dymetylanline and 104.5 g of 1-chloro-3-methylbutene-2 is left to stand at room temperature for 5 days. Crushed crystals are washed with 200 ml of dry
эфира и высушивают в вакууме до посто нного веса. Получают 221 г (0,98 моль; 98%) светлых , гигроскопичных кристаллов с т. пл. 46° С.ether and vacuum dry to constant weight. Obtain 221 g (0.98 mol; 98%) bright, hygroscopic crystals with so pl. 46 ° C
Найдено, %: С1 15,58.Found%: C1 15.58.
CnHaoClN.CnHaoClN.
Вычислено, %: С1 15,74.Calculated,%: C1 15.74.
Препарат очень хорошо раствор етс в воде , спирте, ацетонитриле.The drug is very soluble in water, alcohol, and acetonitrile.
Пример 2. Разложение препарата при нагревании .Example 2. The decomposition of the drug when heated.
22,55 г хлористого диметилфенил-(3-метилбутен-2-ил ) аммони нагревают при 50° С в течение 6 мин.. Соль частично плавитс и расслаиваетс . После быстрого охлаждени жидкую часть подкисл ют сол ной кислотой и экстрагируют эфиром. После отгонки эфира получают 5 г (50%) 1-хлор-3-метилбутена-2 с т. кип. 103-107° С, п 1,4395.22.55 g of dimethylphenyl (3-methylbuten-2-yl) ammonium chloride is heated at 50 ° C for 6 minutes. The salt is partially melted and exfoliated. After rapid cooling, the liquid portion is acidified with hydrochloric acid and extracted with ether. After distilling off the ester, 5 g (50%) of 1-chloro-3-methyl butene-2 are obtained with a boil. 103-107 ° C, p 1.4395.
Подщелачиванием сол нокислого сло , экстрагированием эфиром получают 6 г (50%) диметиланилина с т. кип. 60-62° С/7 мм. рт. ст.; п 1,5580. Пикрат плавитс при 155° С и не дает депрессии температуры плавлени в смеси с известным образцом.Alkalinization of the hydrochloric acid layer, extraction with ether gives 6 g (50%) of dimethylaniline with m.p. 60-62 ° C / 7 mm. Hg v .; p 1.5580. The picrate melts at 155 ° C and does not depress the melting point in a mixture with a known sample.
-Предмет изо-бретени 3 взаимодействию с хлоргидратом изопрена в нормальных услови х с последующим выделе4 нием целевого продукта путем промывки реакционной массы эфиром и вакуум-сушки.- Subject of the third interaction with isoprene chlorohydrate under normal conditions with the subsequent isolation of the target product by washing the reaction mixture with ether and vacuum drying.
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU293793A1 true SU293793A1 (en) |
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