SU234415A1 - METHOD FOR PRODUCING 1,3-TIAZANE DERIVATIVES - Google Patents
METHOD FOR PRODUCING 1,3-TIAZANE DERIVATIVESInfo
- Publication number
- SU234415A1 SU234415A1 SU1185715A SU1185715A SU234415A1 SU 234415 A1 SU234415 A1 SU 234415A1 SU 1185715 A SU1185715 A SU 1185715A SU 1185715 A SU1185715 A SU 1185715A SU 234415 A1 SU234415 A1 SU 234415A1
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- derivatives
- tiazane
- producing
- hydrazone
- acid
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 13
- 239000002253 acid Substances 0.000 claims description 4
- VMHLLURERBWHNL-UHFFFAOYSA-M sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 claims description 4
- 238000009835 boiling Methods 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 3
- 150000007513 acids Chemical class 0.000 claims description 2
- 150000003934 aromatic aldehydes Chemical class 0.000 claims description 2
- 125000003968 arylidene group Chemical group [H]C(c)=* 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000004435 hydrogen atoms Chemical group [H]* 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 239000011780 sodium chloride Substances 0.000 claims description 2
- -1 for example Substances 0.000 claims 1
- 238000000926 separation method Methods 0.000 claims 1
- 238000004458 analytical method Methods 0.000 description 6
- 229960000583 Acetic Acid Drugs 0.000 description 4
- 229940040526 Anhydrous Sodium Acetate Drugs 0.000 description 2
- FOCAUTSVDIKZOP-UHFFFAOYSA-N Chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- RTKKIGMVORMMCH-UHFFFAOYSA-N 1-nitrocyclohexa-2,4-diene-1-carbaldehyde Chemical compound [O-][N+](=O)C1(C=O)CC=CC=C1 RTKKIGMVORMMCH-UHFFFAOYSA-N 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 238000005020 pharmaceutical industry Methods 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Description
Изобретение относитс к способу получени новых соединений, которые могут найти применение в фармацевтической промышленности и в качестве физиологически активных веществ .This invention relates to a process for the preparation of new compounds that can be used in the pharmaceutical industry and as physiologically active substances.
Предложен способ лолучени производных 1,3-тиазана общей формулыA method is proposed for the production of 1,3-thiazan derivatives of the general formula
N-NNn
№5 №5
где R - водород, арилиден.where R is hydrogen, arylidene.
Способ заключаетс в том, что 4-тио-1,3-тиазанон-2-тиосемикарбазон-4 подвергают конденсации с монохлоруксусной кислотой в среде органического растворител , например леДЯ1НОЙ уксусной кислоты, в присутствии солей слабых кислот, напри.мер ацетата натри , при тем пературе кипени реакционной массы. Процесс ведут в присутствии ароматических альдегидов .The method consists in that 4-thio-1,3-thiazanon-2-thiosemicarbazone-4 is condensed with monochloroacetic acid in an organic solvent medium, for example, injecting acetic acid, in the presence of salts of weak acids, for example sodium acetate, with boiling point of the reaction mass. The process is conducted in the presence of aromatic aldehydes.
Продукты выдел ют известным способом.Products are isolated in a known manner.
Выход составл ет 15,8-41,9 /окислоты , 1,0 г безводного ацетата натри ц 10 мл лед ной уксусной кислоты нагревают в колбе с обратным холодильником. Смесь кип т т в течение 4 час. noCvie охлаждени образовавшийс осадок отфильтровывают, промывают уксусной кислотой и водой. Получают 0,2 г тиазолидиндион-2,4-2-оксо-Г,3-тиазанилиден-4-гидразона-2 с т. пл. 231-232°С. Элементарный анализ, о/о: N 23,15; S 25,80.The yield is 15.8-41.9 / acid, 1.0 g of anhydrous sodium acetate and 10 ml of glacial acetic acid are heated in a flask under reflux. The mixture was boiled for 4 hours. noCvie cooling the precipitate is filtered off, washed with acetic acid and water. Obtain 0.2 g of thiazolidinedione-2,4-2-oxo-G, 3-thiazanilidene-4-hydrazone-2 with so pl. 231-232 ° C. Elementary analysis, o / o: N 23.15; S 25.80.
C7H8N4O.Sa.C7H8N4O.Sa.
Вычислено, /о: N 22,94; S 26,25.Calculated / a: N 22.94; S 26.25.
Пример 2. Смесь 1,02 г 4-тио-1,3-тиазанон-2-тиосемикарбазона-4 ,1, 42 г монохлоруксусной кислоты, 1,23 г безводного ацетата натри , 2,26 г /1-нитробензальдегида и 40 мл уксусной кислоты кип т т в течение 5гос в колбе с обратным холодильником. После охлаждени реакционную смесь разбавл ют водой и отфильтровывают 5,5-ди-/г--нитробензилидентиазолиДиндцон-2 ,4-1,3-тиазанилиден - 4-он-2гидразона-2 с т. лл. 135-138°С (из спирта).Example 2. A mixture of 1.02 g of 4-thio-1,3-thiazanon-2-thiosemicarbazone-4, 1, 42 g of monochloroacetic acid, 1.23 g of anhydrous sodium acetate, 2.26 g / 1-nitrobenzaldehyde and 40 ml acetic acid is refluxed for 5h in a flask. After cooling, the reaction mixture is diluted with water and 5,5-di- / g-nitrobenzylidentiazol Dindone-2, 4-1,3-thiazanylidene-4-one-2 hydrazone-2 is filtered off with a liter. 135-138 ° C (from alcohol).
Выход продукта, 41,8. Элементарный анализ, %: N 15,98; S 12,24. Со ПиХбОбЗо.The product yield, 41,8. Elementary analysis,%: N 15,98; S 12.24. With PiHBOZO.
Вычислено, о/о; N 16,46 и S 12,56. Аналогично получают с-выходом 29,0% 5,5дифурфурилидентиазолидиндион-2 ,4-1,3 - тиазанилиден-4-он-2-гидразон-2 с т. пл. 105- 108°С.Calculated o / o; N 16.46 and S 12.56. Similarly, a yield of 29.0% of 5.5 diflufurylidentiazolidinedione-2, 4-1.3 - thiazanilidene-4-one-2-hydrazone-2 with a melting point is obtained. 105-108 ° C.
Элементарный анализ, о/о: N 13,77; S 15,82. CnHoaNiOiSs.Elementary analysis, o / o: N 13.77; S 15.82. CnHoaNiOiSs.
Вычислено, %: N 13,99; S 16,01 (с выходом 15,80/0 5,5-ди-/г-метоксибензилидентиазолидиндион-2 ,4-1,3 - тиазалилиден-4-он-2-гидразона-2 ) ст. пл. 108-115°С.Calculated,%: N 13.99; S 16.01 (with the yield of 15.80 / 0 5,5-di- / g-methoxybenzylidentiazolidinedione-2, 4-1.3 - thiazalylidene-4-one-2-hydrazone-2) Art. square 108-115 ° C.
Элементарный анализ, о/о: N 12,07; S 13,26.Elementary analysis, o / o: N 12.07; S 13.26.
С2зН20 4О452.С2зН20 4О452.
Вычислено, %: N 11,66; S 13,34 (с выходом 31,б)/о 5,5-ди-/г-диметиламинобензилидентиазолидиндион- ,2,4-1,3-тиазанилиден-4-он-2 - гидразона-2 ) с т. пл. 92-98°С.Calculated,%: N 11.66; S 13.34 (with the release of 31, b) / about 5,5-di- / g-dimethylaminobenzylidentiazolidinedione-, 2,4-1,3-thiazanilidene-4-one-2 - hydrazone-2) with m. Pl. 92-98 ° C.
Элементарный анализ, %: N 16,54; S 13,20.Elementary analysis,%: N 16,54; S 13.20.
С2оН2бНбО252.C2H2bNbO252.
Вычислено, о/о: N 16,59; S 12,66 (с выходом 33,2% 5,5 - дивалилидентиазолидиндион - 2,41 ,3-он-2-тиазанилиден-4-гидразона-2) с т. пл. 102-107°С.Calculated, o / o: N 16,59; S 12.66 (with a yield of 33.2% 5.5 - divalylidentiazolidinedione - 2.41, 3-one-2-thiazanilidene-4-hydrazone-2) with m. Pl. 102-107 ° C.
Элементарный анализ, N 11,03; S 12,47.Elementary analysis, N 11.03; S 12.47.
С2зН2оМ4Об52.С2зН2оМ4Об52.
Вычислено, %: N Ш,93; S 12,51.Calculated,%: N W, 93; S 12,51.
Предмет изобретени Subject invention
Claims (2)
Publications (1)
| Publication Number | Publication Date |
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| SU234415A1 true SU234415A1 (en) |
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