SU263597A1 - METHOD OF OBTAINING 3-ALKYLAMINO-4-CARBETOXI-5-METHYL THIOPHENE - Google Patents
METHOD OF OBTAINING 3-ALKYLAMINO-4-CARBETOXI-5-METHYL THIOPHENEInfo
- Publication number
- SU263597A1 SU263597A1 SU1284573A SU1284573A SU263597A1 SU 263597 A1 SU263597 A1 SU 263597A1 SU 1284573 A SU1284573 A SU 1284573A SU 1284573 A SU1284573 A SU 1284573A SU 263597 A1 SU263597 A1 SU 263597A1
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- alkylamino
- carbethoxy
- carbetoxi
- obtaining
- methylthiophene
- Prior art date
Links
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- ZQPCKKGNETVBMN-UHFFFAOYSA-N ethyl 4-hydroxy-2-methylthiophene-3-carboxylate Chemical compound CCOC(=O)C1=C(C)SC=C1O ZQPCKKGNETVBMN-UHFFFAOYSA-N 0.000 description 3
- -1 3-methylamino-4-carbethoxy-5-methylthiophene Chemical compound 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L mgso4 Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 235000005985 organic acids Nutrition 0.000 description 2
- 150000003141 primary amines Chemical class 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- DDQAGDLHARKUFX-UHFFFAOYSA-N acetic acid;methanamine Chemical compound [NH3+]C.CC([O-])=O DDQAGDLHARKUFX-UHFFFAOYSA-N 0.000 description 1
- MPPQYFREIJCHTB-UHFFFAOYSA-N acetic acid;phenylmethanamine Chemical compound CC([O-])=O.[NH3+]CC1=CC=CC=C1 MPPQYFREIJCHTB-UHFFFAOYSA-N 0.000 description 1
- 125000005210 alkyl ammonium group Chemical group 0.000 description 1
- 235000019257 ammonium acetate Nutrition 0.000 description 1
- LXTKCTMGEWVPTB-UHFFFAOYSA-N butylazanium;acetate Chemical compound CC(O)=O.CCCCN LXTKCTMGEWVPTB-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 150000003233 pyrroles Chemical class 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
Description
Предлагают способ получени 3-алкиламино-4-карбэтокси-5-метилтиофенов .A method for the preparation of 3-alkylamino-4-carbethoxy-5-methylthiophenes is proposed.
З-Алкиламино-4-карбэтокси - 5 - метилтиофены в литературе не описаны. На их основе возможен синтез конденсированных гетероциклических систем, например тиено-(3,2-Ь)пирролов , которые представл ют интерес в плане поиска биологически активных веществ.3-Alkylamino-4-carbethoxy-5-methylthiophenes are not described in the literature. Based on them, it is possible to synthesize condensed heterocyclic systems, for example, thieno- (3,2-b) pyrroles, which are of interest in the search for biologically active substances.
В соответствии с предлагаемым способом 3-алкиламино - 4 - карбэтокси - 5-метилтиофены получают путем непродолжительного нагревани 3-окси-4-карбэтокси-5-метилтиофена с сол ми первичных аминов с органическими кислотами , например с ацетатами алкиламмони , при температуре не выше 120-130°С, и конечный продукт выдел ют известным способом . Выход алкиламинотиофенов составл ет 69-86%:In accordance with the proposed method, 3-alkylamino-4-carbethoxy-5-methylthiophenes are obtained by briefly heating 3-hydroxy-4-carbethoxy-5-methylthiophene with salts of primary amines with organic acids, for example, with alkyl ammonium acetates, at a temperature not exceeding 120 -130 ° C, and the final product is isolated in a known manner. The yield of alkylaminothiophenes is 69-86%:
Пример 1. 3-Метилам ино-4-карбэтокси-5метилтиофен .Example 1. 3-Methylamine-4-carbethoxy-5methylthiophene.
Нагревают 4,7 г (0,025 моль) З-окси-4-карбэтокси-5-метилтиофена с 46 г (0,5 моль) ацетата метиламмони при перемешивании в течение 10 мин, при 120-130°С. Реакционную смесь выливают в 100 мл лед ной воды. Выпавший осадок отдел ют и промывают на фильтре водой. Выход З-метиламино-4-карбэтокси-5-метилтиофена 4,3 г (86%), т. пл. 37-ЗЗХ (из метанола).4.7 g (0.025 mol) of 3-hydroxy-4-carbethoxy-5-methylthiophene are heated with 46 g (0.5 mol) of methyl ammonium acetate with stirring for 10 minutes at 120-130 ° C. The reaction mixture was poured into 100 ml of ice water. The precipitate formed is separated and washed on the filter with water. The output of the 3-methylamino-4-carbethoxy-5-methylthiophene 4.3 g (86%), so pl. 37-ЗЗХ (from methanol).
Найдено, %: С 54,45; 54,23; Н 6,70; 6,47: N 17,12; 7,26; S 16,12; 16,36.Found,%: C 54.45; 54.23; H 6.70; 6.47: N 17.12; 7.26; S 16.12; 16.36.
CgH.sNOjS.CgH.snojs.
Вычислено, %: С 54,24; Н 6,78; N 7,03. S 16,09.Calculated,%: C 54.24; H 6.78; N 7.03. S 16.09.
Пример 2. 3-Бутиламино-4-карбэтОКси-5метилтпофен .Example 2. 3-Butylamino-4-karbetOksi-5metiltpofen.
Дл опыта берут 4,7 г (0,025 моль) 3-окси-4-кар,бэтокси-5-метилтиофена и 65,5 г (0,5 моль) ацетата бутиламмони . Реакцию провод т в услови х примера 1. Реакционную смесь выливают в 100 мл лед ной воды. Образовавшийс в результате реакции 3-бутиламино-4-карбэтокси-5-метилтпофен извлекают эфиром. Эфирный раствор промывают водой и сушат сульфатом магни . Растворитель отгон ют, остаток перегон ют в вакууме. Выход 3-бутилампно-4-карбэтокси-5-метилтиофена 4,2 г (69%); т. кип. 133-134°С (1 мм); 1,5307.For the test, 4.7 g (0.025 mol) of 3-hydroxy-4-cc, betaxy-5-methylthiophene and 65.5 g (0.5 mol) of butylammonium acetate are taken. The reaction was carried out under the conditions of Example 1. The reaction mixture was poured into 100 ml of ice water. The resulting 3-butylamino-4-carbethoxy-5-methyltpophene is recovered by ether. The ether solution is washed with water and dried over magnesium sulfate. The solvent is distilled off, the residue is distilled in vacuo. The yield of 3-butylampno-4-carbethoxy-5-methylthiophene 4.2 g (69%); m.p. 133-134 ° C (1 mm); 1.5307.
Найдено, %: С 59,69; 59,79; Н 7,76; 7,76; N 6,05; 6,06; S 13,12; 13,44.Found,%: C 59.69; 59.79; H 7.76; 7.76; N 6.05; 6.06; S 13.12; 13.44.
Ci2Hi9N02S.Ci2Hi9N02S.
Вычислено, %: С 59,72; Н 7,93; N 5,83: S 13,29.Calculated,%: C 59.72; H 7.93; N 5.83: S 13.29.
ацетата бензиламмони . Реакцию и выделение вещества провод т в услови х примера 2. Выход 3-бензиламино-4-карбэтокси-5-метилтиофена 2,9 г (69%); т. кип. 174-175°С (1 лглг), т. пл. 25-26°С.benzyl ammonium acetate. The reaction and the isolation of the substance were carried out under the conditions of Example 2. The yield of 3-benzylamino-4-carbethoxy-5-methylthiophene was 2.9 g (69%); m.p. 174-175 ° С (1 лглг), t. Pl. 25-26 ° C.
Найдено, %: С 65,62; 65,82; Н 6,25; 6,34; N 4,97; 5,21; S 11,64; 11,60.Found,%: C 65.62; 65.82; H 6.25; 6.34; N 4.97; 5.21; S 11.64; 11.60.
CisHivNOzS.CisHivNOzS.
Вычислено, %: С 65,43; Н 6,22; N 5,09; S 11,64.Calculated,%: C 65.43; H 6.22; N 5.09; S 11.64.
Предмет изобретени Subject invention
Способ Получени З-алкиламино-4-карбэтокси-5-метилтиофена , отличающийс тем, что 3-окси-4-карбэтоКСи-5-метилтиофен нагревают с сол ми первичных аминов с органическими кислотами, предпочтительно, при температуре не выше .120-130°С, и конечный продукт выдел ют известным способом.The method of preparing 3-alkylamino-4-carbethoxy-5-methylthiophene, characterized in that 3-hydroxy-4-carbethoxy-5-methylthiophene is heated with salts of primary amines with organic acids, preferably at a temperature not higher than 120-130 ° C, and the final product is isolated in a known manner.
Publications (1)
| Publication Number | Publication Date |
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| SU263597A1 true SU263597A1 (en) |
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