SU1298209A1 - Method for producing 3-arensulfonylpropeneamides - Google Patents
Method for producing 3-arensulfonylpropeneamides Download PDFInfo
- Publication number
- SU1298209A1 SU1298209A1 SU853963195A SU3963195A SU1298209A1 SU 1298209 A1 SU1298209 A1 SU 1298209A1 SU 853963195 A SU853963195 A SU 853963195A SU 3963195 A SU3963195 A SU 3963195A SU 1298209 A1 SU1298209 A1 SU 1298209A1
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- formula
- water
- hours
- propinamide
- yield
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title description 2
- 238000000034 method Methods 0.000 claims abstract description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 9
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical class NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims abstract description 6
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 claims abstract description 5
- 239000004327 boric acid Substances 0.000 claims abstract description 5
- 229910052700 potassium Inorganic materials 0.000 claims abstract description 4
- 229910052708 sodium Inorganic materials 0.000 claims abstract description 4
- 239000011734 sodium Substances 0.000 claims abstract description 4
- 229910000403 monosodium phosphate Inorganic materials 0.000 claims abstract description 3
- 235000019799 monosodium phosphate Nutrition 0.000 claims abstract description 3
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 claims abstract description 3
- 239000002904 solvent Substances 0.000 claims abstract 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims abstract 4
- 150000001875 compounds Chemical class 0.000 claims description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 6
- 239000000047 product Substances 0.000 claims description 6
- 230000003993 interaction Effects 0.000 claims description 4
- 239000012736 aqueous medium Substances 0.000 claims description 3
- 235000019738 Limestone Nutrition 0.000 claims description 2
- 150000001408 amides Chemical class 0.000 claims description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-M dihydrogenphosphate Chemical compound OP(O)([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-M 0.000 claims description 2
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 claims description 2
- 239000006028 limestone Substances 0.000 claims description 2
- 239000002244 precipitate Substances 0.000 claims description 2
- 239000011541 reaction mixture Substances 0.000 claims description 2
- 238000003756 stirring Methods 0.000 claims description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims 2
- 229910052783 alkali metal Inorganic materials 0.000 claims 2
- 150000001340 alkali metals Chemical class 0.000 claims 2
- XLYOFNOQVPJJNP-PWCQTSIFSA-N Tritiated water Chemical compound [3H]O[3H] XLYOFNOQVPJJNP-PWCQTSIFSA-N 0.000 claims 1
- 238000000605 extraction Methods 0.000 claims 1
- 238000001914 filtration Methods 0.000 claims 1
- 229910052753 mercury Inorganic materials 0.000 claims 1
- JGGFVSGYTHUAOQ-UHFFFAOYSA-M sodium;naphthalene-2-sulfinate Chemical compound [Na+].C1=CC=CC2=CC(S(=O)[O-])=CC=C21 JGGFVSGYTHUAOQ-UHFFFAOYSA-M 0.000 claims 1
- 238000001228 spectrum Methods 0.000 claims 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 1
- 239000003814 drug Substances 0.000 abstract description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 abstract 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical group [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 abstract 1
- 239000000654 additive Substances 0.000 abstract 1
- 239000011591 potassium Substances 0.000 abstract 1
- NVBFHJWHLNUMCV-UHFFFAOYSA-N sulfamide Chemical class NS(N)(=O)=O NVBFHJWHLNUMCV-UHFFFAOYSA-N 0.000 abstract 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- 238000004566 IR spectroscopy Methods 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-L Phosphate ion(2-) Chemical compound OP([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-L 0.000 description 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- CHLCPTJLUJHDBO-UHFFFAOYSA-M sodium;benzenesulfinate Chemical compound [Na+].[O-]S(=O)C1=CC=CC=C1 CHLCPTJLUJHDBO-UHFFFAOYSA-M 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Изобретение касаетс сульфамидов , в частности получени 3-арен- сульфонилпропенамидов (СА) общей формулы Аг S(0) О NH,j, где Аг - З-нитрофенил или 2-децилфенш1, которые как биологические добавки могут быть использованы в медицине, сельском хоз йстве, пищевой промышленности. Упрощение процесса и повышение выхода СА достигаетс использованием пропинамида, который подвергают взаимодействию с аренсульфинатами формулы Ar-S(0),Me, где Me - калий или натрий, в среде воды в качестве растворител , в присутствии эквимол рного количества борной кислоты или дигидрофосфата натри . Способ обеспечивает повьше- ние выхода с 46 до 58%, позвол ет исключить р д операций, св занных с использованием ацетонового растворител , и сократить продолжительность процесса с 40 до 2 ч. 1 табл. i (Л to UD 00 IsD О. QDThe invention relates to sulfamides, in particular the preparation of 3-arenesulfonyl propenamides (CA) of the general formula Ar S (0) O NH, j, where Ar is Z-nitrophenyl or 2-decylfensh1, which as biological additives can be used in medicine, agriculture Food industry. Simplification of the process and an increase in the yield of CA is achieved using propinamide, which is reacted with arensulfinates of the formula Ar-S (0), Me, where Me is potassium or sodium, in a medium of water as a solvent, in the presence of an equimolar amount of boric acid or sodium dihydrogen phosphate. The method provides an increase in yield from 46 to 58%, eliminates a number of operations associated with the use of acetone solvent, and reduces the duration of the process from 40 to 2 hours. Table 1. i (L to UD 00 IsD O. QD
Description
Изобретение относитс к усовершенствованному способу получени 3-арен- сульфонилпропепамидом формулыThe invention relates to an improved process for preparing the 3-arenosulfonylpropamide of formula
ArSO, CONH, (1) где Ar - С,н;, , 3-NO, С Н или , которые могут. быть использованы в медицине, сельском хоз йстве , пии.(евой проь шленности«ArSO, CONH, (1) where Ar is C, n ;, 3-NO, C H or, which may. be used in medicine, agriculture, FDI.
Целью изобретени вл етс упрощение процесса получени 3-аренсуль- фонилпропенамидов и повышение их выходов , что достигаетс взаимодействием соединени (II): ArSO Me, где Ar - имеет указанное значение, Ме- Na или К, с пропинамидом в водной среде и в присутствии эквимол рного количества борной кислоты или гидро- или дигидрофосфата натри .The aim of the invention is to simplify the process of obtaining 3-arensulphonyl propenamides and increase their yields, which is achieved by the interaction of compound (II): ArSO Me, where Ar - has the indicated value, Me — Na or K, with propinamide in an aqueous medium and in the presence of equimole a substantial amount of boric acid or sodium hydro- or dihydrogen phosphate.
Пример 1. К раствору 0,01 мол свежеприготовленного бензолсульфина- та натри в 30 мл воды прибавл ют при перемешивании раствор 0,01 моль борной кислоты в 20 мл воды и далее раствор 0,01 моль пропинамида в 5 мл этанола и 20 мл воды. Реакционную смесь перемешивают при комнатной температуре 2 ч. Через 6 ч осадок целевого продукта отфильтровывают, промывают водой. Продукт можно перекристаллизовывать из изопропилового спир - шаетс до 55-58 против 46% у извест- та или из метанола.Example 1. To a solution of 0.01 mol of freshly prepared sodium benzenesulfinate in 30 ml of water was added with stirring a solution of 0.01 mol of boric acid in 20 ml of water and then a solution of 0.01 mol of propinamide in 5 ml of ethanol and 20 ml of water. The reaction mixture is stirred at room temperature for 2 hours. After 6 hours, the precipitate of the desired product is filtered off, washed with water. The product can be recrystallized from isopropyl alcohol to 55-58 versus 46% in limestone or from methanol.
Вместо борной кислоты молаю использовать эквивалентные количества гидрофосфата или дигидрофосфата натри .Instead of boric acid, I use equivalent amounts of hydrogen phosphate or sodium dihydrogen phosphate.
Таким же образом получают другие амиды, приведенные в таблицеIn the same way receive other amides listed in the table.
В таблице приведены коггстанты, выходы и спектральные свойства 3- -аренсульфопилпропенамидов.The table shows the cohgants, the outputs, and the spectral properties of 3-a-Rensulfopropyl propenamides.
Строение и конфигураци полученных соединений доказаны методами ИК и ЯМР И-спектроскопии.The structure and configuration of the obtained compounds were proved by IR and NMR spectroscopy.
В ИК-спектрах всех соединений присутствуют сигналы, характеризуюного способа.In the IR spectra of all compounds, there are signals characteristic of the method.
Claims (2)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SU853963195A SU1298209A1 (en) | 1985-08-19 | 1985-08-19 | Method for producing 3-arensulfonylpropeneamides |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SU853963195A SU1298209A1 (en) | 1985-08-19 | 1985-08-19 | Method for producing 3-arensulfonylpropeneamides |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU1298209A1 true SU1298209A1 (en) | 1987-03-23 |
Family
ID=21200680
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU853963195A SU1298209A1 (en) | 1985-08-19 | 1985-08-19 | Method for producing 3-arensulfonylpropeneamides |
Country Status (1)
| Country | Link |
|---|---|
| SU (1) | SU1298209A1 (en) |
-
1985
- 1985-08-19 SU SU853963195A patent/SU1298209A1/en active
Non-Patent Citations (1)
| Title |
|---|
| Патент US № 3976668, кл. 260-397.6, опублик. 1976. * |
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