RU2309955C1 - METHOD FOR PREPARING PERHYDRO-5-HYDROXY-1,3,5-DITHIAZINE, β-ETHYLDIHYDRO-1,3,5-DITHIAZINE-5-ETHANOL AND 4-[4H-1,3,5-DITHIAZINE-5(6H)-YL]-1-BUTANOL - Google Patents
METHOD FOR PREPARING PERHYDRO-5-HYDROXY-1,3,5-DITHIAZINE, β-ETHYLDIHYDRO-1,3,5-DITHIAZINE-5-ETHANOL AND 4-[4H-1,3,5-DITHIAZINE-5(6H)-YL]-1-BUTANOL Download PDFInfo
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- RU2309955C1 RU2309955C1 RU2006103161/04A RU2006103161A RU2309955C1 RU 2309955 C1 RU2309955 C1 RU 2309955C1 RU 2006103161/04 A RU2006103161/04 A RU 2006103161/04A RU 2006103161 A RU2006103161 A RU 2006103161A RU 2309955 C1 RU2309955 C1 RU 2309955C1
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- dithiazine
- ethanol
- perhydro
- butanol
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- JBHXYZPAQPANIB-UHFFFAOYSA-N 2-(1,3,5-dithiazinan-5-yl)butan-1-ol Chemical compound CCC(CO)N1CSCSC1 JBHXYZPAQPANIB-UHFFFAOYSA-N 0.000 title claims abstract description 23
- 238000000034 method Methods 0.000 title claims abstract description 18
- NRTZJFHQHHQQQQ-UHFFFAOYSA-N 5-hydroxy-1,3,5-dithiazinane Chemical compound ON1CSCSC1 NRTZJFHQHHQQQQ-UHFFFAOYSA-N 0.000 title claims abstract description 15
- XDWSYLSLBPMANC-UHFFFAOYSA-N 4-(1,3,5-dithiazinan-5-yl)butan-1-ol Chemical compound S1CSCN(C1)CCCCO XDWSYLSLBPMANC-UHFFFAOYSA-N 0.000 title claims abstract description 13
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims abstract description 31
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 claims abstract description 12
- 229910000037 hydrogen sulfide Inorganic materials 0.000 claims abstract description 11
- 239000007864 aqueous solution Substances 0.000 claims abstract description 7
- 229920006395 saturated elastomer Polymers 0.000 claims abstract description 4
- 238000003756 stirring Methods 0.000 claims abstract description 3
- 150000001414 amino alcohols Chemical class 0.000 claims description 6
- 238000003786 synthesis reaction Methods 0.000 abstract description 7
- 230000015572 biosynthetic process Effects 0.000 abstract description 6
- 150000001875 compounds Chemical class 0.000 abstract description 5
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 abstract description 4
- 239000003153 chemical reaction reagent Substances 0.000 abstract description 4
- 230000003993 interaction Effects 0.000 abstract description 4
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 abstract description 3
- 230000000694 effects Effects 0.000 abstract description 3
- 239000002594 sorbent Substances 0.000 abstract description 2
- 239000000126 substance Substances 0.000 abstract 2
- 230000005764 inhibitory process Effects 0.000 abstract 1
- 244000005700 microbiome Species 0.000 abstract 1
- 239000010970 precious metal Substances 0.000 abstract 1
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 8
- MHAKNDMCJAVDTK-UHFFFAOYSA-N 1-(1,3,5-dithiazinan-5-yl)ethanol Chemical compound S1CSCN(C1)C(C)O MHAKNDMCJAVDTK-UHFFFAOYSA-N 0.000 description 5
- HYHCSLBZRBJJCH-UHFFFAOYSA-M sodium hydrosulfide Chemical compound [Na+].[SH-] HYHCSLBZRBJJCH-UHFFFAOYSA-M 0.000 description 5
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N DMSO Substances CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- 238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000001819 mass spectrum Methods 0.000 description 3
- 230000003595 spectral effect Effects 0.000 description 3
- WEMREENHLUWMAJ-UHFFFAOYSA-N 1-(1,3,5-oxathiazinan-5-yl)ethanol Chemical compound O1CSCN(C1)C(C)O WEMREENHLUWMAJ-UHFFFAOYSA-N 0.000 description 2
- GXAFNKBVQWVXTO-UHFFFAOYSA-N 4h-1,3,5-dithiazine Chemical class C1SCN=CS1 GXAFNKBVQWVXTO-UHFFFAOYSA-N 0.000 description 2
- 241000894006 Bacteria Species 0.000 description 2
- -1 ethanolamine) Chemical class 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 2
- ZRKMQKLGEQPLNS-UHFFFAOYSA-N 1-Pentanethiol Chemical class CCCCCS ZRKMQKLGEQPLNS-UHFFFAOYSA-N 0.000 description 1
- LRHPLDYGYMQRHN-UHFFFAOYSA-N 1-butanol Substances CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 1
- FGVOZZVEZUWLRF-UHFFFAOYSA-N CCSCSCCNCCCCO Chemical compound CCSCSCCNCCCCO FGVOZZVEZUWLRF-UHFFFAOYSA-N 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- MNQDKWZEUULFPX-UHFFFAOYSA-M dithiazanine iodide Chemical class [I-].S1C2=CC=CC=C2[N+](CC)=C1C=CC=CC=C1N(CC)C2=CC=CC=C2S1 MNQDKWZEUULFPX-UHFFFAOYSA-M 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000010183 spectrum analysis Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Description
Предлагаемое изобретение относится к органической химии, в частности к способу получения пергидро-5-гидрокси-1,3,5-дитиазина, β-этилдигидро-1,3,5-дитиазин-5-этанола и 4-[4Н-1,3,5-дитиазин-5(6Н)-ил]-1-бутанола общей формулы (1)The present invention relates to organic chemistry, in particular to a method for producing perhydro-5-hydroxy-1,3,5-dithiazine, β-ethyl dihydro-1,3,5-dithiazin-5-ethanol and 4- [4H-1,3 , 5-dithiazin-5 (6H) -yl] -1-butanol of the general formula (1)
R=OH (1a);R = OH (1a);
R=СН(СН2СН3)СН2ОН (1б);R = CH (CH 2 CH 3 ) CH 2 OH (1b);
R=СН2СН2СН2СН2ОН (1в).R = CH 2 CH 2 CH 2 CH 2 OH (1c).
Соединения дитиазинового ряда могут найти применение в качестве селективных сорбентов и экстрагентов, специальных реагентов для подавления жизнедеятельности бактерий в различных средах (от легкой промышленности до нефти), биологически активных веществ по отношению к сульфатредуцирующим бактериям.The compounds of the dithiazine series can be used as selective sorbents and extractants, special reagents for suppressing the activity of bacteria in various media (from light industry to oil), biologically active substances with respect to sulfate-reducing bacteria.
Известен способ (С.Р.Хафизова, В.Р.Ахметова, Л.Ф.Коржова, Т.В.Хакимова, Г.Р.Надыргулова, Р.В.Кунакова, Э.А.Круглов, У.М.Джемилев. Многокомпонентная конденсация алифатических аминов с формальдегидом и сероводородом. Изв. АН. Сер. хим., 2005, 2, 423.) получения производных 1,3,5-дитиазина, в частности 2-пергидро(1,3,5-дитиазин-5-ил)-1-этанола (2) и 2-пергидро(1,3,5-оксатиазин-5-ил)-1-этанола (3) взаимодействием этаноламина с сероводородом и формальдегидом по схемеThe known method (S.R. Khafizova, V.R. Akhmetova, L.F. Korzhova, T.V. Khakimova, G.R. Nadyrgulova, R.V. Kunakova, E.A. Kruglov, U.M. Dzhemilev Multicomponent condensation of aliphatic amines with formaldehyde and hydrogen sulfide. Izv. AN Ser. Chem., 2005, 2, 423.) for the preparation of 1,3,5-dithiazine derivatives, in particular 2-perhydro (1,3,5-dithiazine- 5-yl) -1-ethanol (2) and 2-perhydro (1,3,5-oxathiazin-5-yl) -1-ethanol (3) by the interaction of ethanolamine with hydrogen sulfide and formaldehyde according to the scheme
Известный способ не позволяет получать пергидро-5-гидрокси-4Н-1,3,5-дитиазин (1а), β-этилдигидро-4Н-1,3,5-дитиазин-5-этанол (1б) и 4-[4Н-1,3,5-дитиазин-5(6Н)-ил]-1-бутанол (1в).The known method does not allow to obtain perhydro-5-hydroxy-4H-1,3,5-dithiazine (1a), β-ethyl dihydro-4H-1,3,5-dithiazine-5-ethanol (1b) and 4- [4H- 1,3,5-dithiazin-5 (6H) -yl] -1-butanol (1c).
Известен способ (Deutsche Gold- und Silber-Scheideanstalt vormals Roessler. F.P. 1, 341, 792/1963 (Chem. Abs., 1964, 60, 5528d)) получения производных 1,3,5-дитиазина, в частности 2-пергидро(1,3,5-дитиазин-5-ил)-1-этанола (2), взаимодействием гидросульфида натрия (NaHS) с этаноламином и формальдегидом по схемеA known method (Deutsche Gold- und Silber-Scheideanstalt vormals Roessler. FP 1, 341, 792/1963 (Chem. Abs., 1964, 60, 5528d)) for obtaining derivatives of 1,3,5-dithiazine, in particular 2-perhydro ( 1,3,5-dithiazin-5-yl) -1-ethanol (2), by the interaction of sodium hydrosulfide (NaHS) with ethanolamine and formaldehyde according to the scheme
Известный способ не позволяет получать пергидро-5-гидрокси-4Н-1,3,5-дитиазин (1а), β-этилдигидро-4Н-1,3,5-дитиазин-5-этанол (1б) и 4-[4Н-1,3,5-дитиазин-5(6Н)-ил]-1-бутанол (1в). Данным способом получен 2-пергидро(1,3,5-дитиазин-5-ил)-1-этанол (2) на основе дорогостоящего и высокочистого гидросульфита натрия, который получают из сероводорода и этилата натрия.The known method does not allow to obtain perhydro-5-hydroxy-4H-1,3,5-dithiazine (1a), β-ethyl dihydro-4H-1,3,5-dithiazine-5-ethanol (1b) and 4- [4H- 1,3,5-dithiazin-5 (6H) -yl] -1-butanol (1c). In this way, 2-perhydro (1,3,5-dithiazin-5-yl) -1-ethanol (2) is obtained on the basis of expensive and highly pure sodium hydrosulfite, which is obtained from hydrogen sulfide and sodium ethylate.
Таким образом, в литературе отсутствуют сведения о получении пергидро-5-гидрокси-4Н-1,3,5-дитиазина (1а), β-этилдигидро-4Н-1,3,5-дитиазин-5-этанола (1б) и 4-[4Н-1,3,5-дитиазин-5(6Н)-ил]-1-бутанола (1в).Thus, there is no information in the literature on the preparation of perhydro-5-hydroxy-4H-1,3,5-dithiazine (1a), β-ethyldihydro-4H-1,3,5-dithiazine-5-ethanol (1b) and 4 - [4H-1,3,5-dithiazin-5 (6H) -yl] -1-butanol (1B).
Предлагается новый способ синтеза пергидро-5-гидрокси-4Н-1,3,5-дитиазина (1а), β-этилдигидро-4Н-1,3,5-дитиазин-5-этанола (1б) и 4-[4Н-1,3,5-дитиазин-5(6Н)-ил]-1-бутанола (1в).A new method is proposed for the synthesis of perhydro-5-hydroxy-4H-1,3,5-dithiazine (1a), β-ethyldihydro-4H-1,3,5-dithiazine-5-ethanol (1b) and 4- [4H-1 3,5-dithiazin-5 (6H) -yl] -1-butanol (1c).
Сущность метода заключается во взаимодействии насыщенного сероводородом водного раствора формальдегида (37%) с водным раствором аминоспирта общей формулы R-NH2, где R=ОН (1a); СН(СН2СН3)СН2ОН (1б); CH2CH2CH2CH2OH (1в), взятыми в мольном соотношении аминоспирт : формальдегид : сероводород =1:3:2, при комнатной температуре (20-21°С) и перемешивании в течении 3 часов. Образуется пергидро-5-гидрокси-4Н-1,3,5-дитиазин (1а) или при использовании 2-бутаноламина образуется β-этилдигидро-4Н-1,3,5-дитиазин-5-этанол (1б), а при использовании 4-бутаноламина образуется 4-[4Н-1,3,5-дитиазин-5(6Н)-ил]-1-бутанол (1в). Реакция протекает по схемеThe essence of the method consists in the interaction of an aqueous solution of formaldehyde saturated with hydrogen sulfide (37%) with an aqueous solution of an amino alcohol of the general formula R-NH 2 , where R = OH (1a); CH (CH 2 CH 3 ) CH 2 OH (1b); CH 2 CH 2 CH 2 CH 2 OH (1B), taken in the molar ratio of amino alcohol: formaldehyde: hydrogen sulfide = 1: 3: 2, at room temperature (20-21 ° C) and stirring for 3 hours. Perhydro-5-hydroxy-4H-1,3,5-dithiazine (1a) is formed, or when 2-butanolamine is used, β-ethyldihydro-4H-1,3,5-dithiazin-5-ethanol is formed (1b), and when using 4-butanolamine 4- [4H-1,3,5-dithiazin-5 (6H) -yl] -1-butanol is formed (1c). The reaction proceeds according to the scheme.
где R=ОН (1а); СН(СН2СН3)СН2ОН (1б); СН2СН2СН2СН2ОН (1в).where R = OH (1a); CH (CH 2 CH 3 ) CH 2 OH (1b); CH 2 CH 2 CH 2 CH 2 OH (1c).
Целевые продукты - пергидро-5-гидрокси-4Н-1,3,5-дитиазин (1а), β-этилдигидро-4Н-1,3,5-дитиазин-5-этанол (1б) и 4-[4Н-1,3,5-дитиазин-5(6Н)-ил]-1-бутанол (1в) образуются только лишь с участием гидроксиламина (2-бутаноламина), формалина и сероводорода. В присутствии других производных аминоспиртов (например, этаноламина), других альдегидов (например, уксусного, пропионового), других меркаптанов (например, этил или амилмеркаптаны) целевые продукты (1) не образуются. Реакции проводили при комнатной температуре (20-21°С). При более высокой температуре не наблюдается существенного увеличения выхода целевых продуктов, а при меньшей температуре (например, 0°С) снижается скорость реакции.Target products are perhydro-5-hydroxy-4H-1,3,5-dithiazine (1a), β-ethyl dihydro-4H-1,3,5-dithiazine-5-ethanol (1b) and 4- [4H-1, 3,5-dithiazin-5 (6H) -yl] -1-butanol (1c) is formed only with the participation of hydroxylamine (2-butanolamine), formalin and hydrogen sulfide. In the presence of other derivatives of amino alcohols (e.g., ethanolamine), other aldehydes (e.g., acetic, propionic), other mercaptans (e.g. ethyl or amyl mercaptans), the desired products (1) are not formed. The reactions were carried out at room temperature (20-21 ° C). At a higher temperature, there is no significant increase in the yield of the target products, and at a lower temperature (for example, 0 ° C), the reaction rate decreases.
Изменение соотношения исходных реагентов в сторону увеличения содержания формалина по отношению к аминоспирту не приводит к повышению выхода целевых продуктов (1).A change in the ratio of the starting reagents in the direction of increasing the formalin content with respect to the amino alcohol does not increase the yield of the target products (1).
Существенные отличия предлагаемого способаSignificant differences of the proposed method
В предлагаемом способе в качестве исходных соединений используются гидроксиламин, 2-бутаноламин и 4-бутаноламин, в известном способе в качестве исходного реагента применяют этаноламин и дорогостоящий, высокочистый гидросульфид натрия (NaHS), который, как известно, получают из сероводорода и этилата натрия.In the proposed method, hydroxylamine, 2-butanolamine and 4-butanolamine are used as starting compounds, in the known method, ethanolamine and expensive, high-purity sodium hydrosulfide (NaHS), which is known to be obtained from hydrogen sulfide and sodium ethylate, are used as starting reagent.
Преимущества предлагаемого способаThe advantages of the proposed method
Способ позволяет получать с высокой региоселективностью пергидро-5-гидрокси-4Н-1,3,5-дитиазин (1а), β-этилдигидро-4Н-1,3,5-дитиазин-5-этанол (1б) и 4-[4Н-1,3,5-дитиазин-5(6Н)-ил]-1-бутанол (1в), синтез которых в литературе не описан. Разработанный нами метод отличается простотой проведения эксперимента и не требует применения дорогостоящего и высокоочищенного гидросульфида натрия.The method allows to obtain with high regioselectivity perhydro-5-hydroxy-4H-1,3,5-dithiazine (1a), β-ethyl dihydro-4H-1,3,5-dithiazine-5-ethanol (1b) and 4- [4H -1,3,5-dithiazin-5 (6H) -yl] -1-butanol (1c), the synthesis of which is not described in the literature. The method we developed is notable for the simplicity of the experiment and does not require the use of expensive and highly purified sodium hydrosulfide.
Способ поясняется примерами.The method is illustrated by examples.
ПРИМЕР 1. В стеклянный реактор, снабженный механической мешалкой, обратным холодильником, газоподводящей трубкой и капельной воронкой, при комнатной (20-21°С) температуре помещают 3 моля формалина (37% водный раствор), барботированием насыщают раствор формалина сероводородом в течение 30 мин, прикапывают 1 моль солянокислого гидроксиламина в воде, перемешивают 3 ч. При 20-21°С выделяют 5-гидрокси-4Н-1,3,5-дитиазин (1а) с выходом 47%.EXAMPLE 1. In a glass reactor equipped with a mechanical stirrer, reflux condenser, gas supply tube and dropping funnel, 3 moles of formalin (37% aqueous solution) are placed at room temperature (20-21 ° C), and the formalin solution is saturated with hydrogen sulfide for 30 minutes by bubbling 1 drop of 1 mol of hydroxylamine hydrochloride in water is added dropwise, stirred for 3 hours. At 20-21 ° C, 5-hydroxy-4H-1,3,5-dithiazine (1a) is isolated in 47% yield.
Спектральные характеристики (спектры ЯМР1Н зарегистрированы на спектрометре «Bruker АМ-300» (300 МГц) и «Tesla BS-487» (100 МГц), ЯМР 13С - на спектрометре «Jeol FX 90Q» (89,55 и 22,50 МГц), внутренний стандарт ТМС, растворитель CDCI3 и d6-ДМСО. Хромато-масс-спектральный анализ соединений проводили на приборе Finigan 4021) 5-гидрокси-4-Н-1,3,5-дитиазина (1а):Spectral characteristics ( 1 H NMR spectra were recorded on a Bruker AM-300 spectrometer (300 MHz) and Tesla BS-487 (100 MHz), 13 C NMR on a Jeol FX 90Q spectrometer (89.55 and 22, 50 MHz), internal standard TMS, solvent CDCI 3 and d 6 -DMSO. Chromatography-mass spectral analysis of the compounds was performed on a Finigan 4021) 5-hydroxy-4-H-1,3,5-dithiazine (1a) instrument:
ПРИМЕР 2. Аналогичным способом из 2-бутаноламина получают β-этилдигидро-4Н-1,3,5-дитиазин-5-этанол (1б) с выходом 58%.EXAMPLE 2. In a similar manner, β-ethyldihydro-4H-1,3,5-dithiazin-5-ethanol (1b) is obtained from 2-butanolamine in 58% yield.
Спектральные характеристики β-этилдигидро-4Н-1,3,5-дитиазин-5-этанола (1б):Spectral characteristics of β-ethyldihydro-4H-1,3,5-dithiazin-5-ethanol (1b):
ПРИМЕР 3. Аналогичным способом из 4-бутаноламина получают -4-[4-1,3,5-дитиазин-5(6Н)-ил]-1-бутанол (1в) с выходом 51%.EXAMPLE 3. In a similar manner from-4-butanolamine receive -4- [4-1,3,5-dithiazin-5 (6H) -yl] -1-butanol (1B) with a yield of 51%.
Спектральные характеристики 4-бутаноламина-4-[4Н-1,3,5-дитиазин-5(6Н)-ил]-1-бутанола (1в):Spectral characteristics of 4-butanolamine-4- [4H-1,3,5-dithiazin-5 (6H) -yl] -1-butanol (1c):
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| RU2006103161/04A RU2309955C1 (en) | 2006-02-03 | 2006-02-03 | METHOD FOR PREPARING PERHYDRO-5-HYDROXY-1,3,5-DITHIAZINE, β-ETHYLDIHYDRO-1,3,5-DITHIAZINE-5-ETHANOL AND 4-[4H-1,3,5-DITHIAZINE-5(6H)-YL]-1-BUTANOL |
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| RU (1) | RU2309955C1 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2368603C2 (en) * | 2007-08-27 | 2009-09-27 | Институт нефтехимии и катализа РАН | METHOD OF OBTAINING 5-(n-ETHYLCARBOXYPHENYL)-, 5-(n-β-DIETHYLAMINOETHYLCARBOXYPHENYL)- AND 5-(n-SULPHACETAMIDEPHENYL)-1,3,5-DITHIAZINANES |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2160233C1 (en) * | 1999-07-14 | 2000-12-10 | Институт нефтехимии и катализа АН РБ и УНЦ РАН | Agent for suppressing growth of sulfate-reducing bacteria |
-
2006
- 2006-02-03 RU RU2006103161/04A patent/RU2309955C1/en not_active IP Right Cessation
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2160233C1 (en) * | 1999-07-14 | 2000-12-10 | Институт нефтехимии и катализа АН РБ и УНЦ РАН | Agent for suppressing growth of sulfate-reducing bacteria |
Non-Patent Citations (1)
| Title |
|---|
| пример 1. ХАФИЗОВА С.Р. и др. Многокомпонентная конденсация алифатических аминов с формальдегидом и сероводородом, Изв. АН, Сер. хим., 2005, 2, с.423. * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2368603C2 (en) * | 2007-08-27 | 2009-09-27 | Институт нефтехимии и катализа РАН | METHOD OF OBTAINING 5-(n-ETHYLCARBOXYPHENYL)-, 5-(n-β-DIETHYLAMINOETHYLCARBOXYPHENYL)- AND 5-(n-SULPHACETAMIDEPHENYL)-1,3,5-DITHIAZINANES |
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| Publication number | Publication date |
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| RU2006103161A (en) | 2007-08-20 |
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