SU31437A1 - The method of obtaining allylamine salicylacetic acid - Google Patents
The method of obtaining allylamine salicylacetic acidInfo
- Publication number
- SU31437A1 SU31437A1 SU123802A SU123802A SU31437A1 SU 31437 A1 SU31437 A1 SU 31437A1 SU 123802 A SU123802 A SU 123802A SU 123802 A SU123802 A SU 123802A SU 31437 A1 SU31437 A1 SU 31437A1
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- acid
- salicylacetic
- allylamine
- obtaining
- amide
- Prior art date
Links
- JLLXSRLEXBECPY-UHFFFAOYSA-N 2-(carboxymethoxy)benzoic acid Chemical compound OC(=O)COC1=CC=CC=C1C(O)=O JLLXSRLEXBECPY-UHFFFAOYSA-N 0.000 title description 3
- 238000000034 method Methods 0.000 title description 2
- VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 title 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- ABBZJHFBQXYTLU-UHFFFAOYSA-N but-3-enamide Chemical compound NC(=O)CC=C ABBZJHFBQXYTLU-UHFFFAOYSA-N 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 2
- -1 ethyl amide salicylacetate Chemical compound 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 2
- 150000003388 sodium compounds Chemical class 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 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
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
ОСНгСООСзНа + Вг СНг СН -СНз- СеН CONHNa OCHaCOOISa NaOH- QHi CONH-CH2-CH OCHnCOOC3Na + BrH CHg CH -CH3-CeH CONHNa OCHaCOOISa NaOH-QHi CONH-CH2-CH
Реакци проходит с выходами достигающими 80% на исходный эфир.The reaction takes place with yields reaching 80% on the starting ester.
Пример. В 5-литровую колбу с мешалкой и обратным холодильником загружают 2,5 литра сухого бензола, 92 г распыленного металлического тчатри и 89 г этилового эфира амидсалицилуксусной кислоты.Example. A 5-liter flask with a stirrer and reflux condenser is charged with 2.5 liters of dry benzene, 92 g of a sprayed metallic metal and 89 g of ethyl amide salicylacetate.
Смесь кип т т при помешивании несколько часов до окончани выделени водорода. Реакционна смесь п ринимаетThe mixture is boiled while stirring for several hours until the evolution of hydrogen is complete. The reaction mixture takes
182)182)
темно-зеленое окрашивание (цвет натриевого соединени ).dark green color (color of sodium compound).
По окончании выделени водорода прибавл ют 600 г бромистого аллила к продолжают кип чение при помешивании до перехода зеленой окраски в желтый однородный цвет, на что требуетс около 10 часов. Бензольный раствор отдел ют от выпавшего осадка бромистого натри и непрореагировавшего исходного продукта и сгущают на всДй ОСНз COOCgHs ЧомнсНз-сн сн, НС1ОСНгСООН - СбН4 СОМН-СН2-СН СКг CH2At the end of the evolution of hydrogen, 600 g of allyl bromide is added to the boiling, with stirring, until the green color turns to a yellow uniform color, which takes about 10 hours. The benzene solution is separated from the precipitated sodium bromide and unreacted starting material and thickened on the basis of COOCgHs COOCgHs CnOnSn-cf, HC1OHNCOOH - CbH4 COOH-CH2-CH2 CgH2
пой бане; в остатке этиловый эфир аллиламидсалицилуксусной кислоты.sing bath; in the residue ethyl ester of allyl-amide salicylacetic acid.
OCHjCOOQHi. «OCHjCOOQHi. "
СОННСНг-СН СН2 Полученный продукт омыл ют на холоду 10%-ной щелочью и разбавленной сол ной или серной кислотой осаждают аллиламидсалицилуксусную кислоту, отсасывают , промывают водой и перекристаллизовывают из спирта. Получаетс продукт с т. пл. 120- 121°.СОННСНг-СН2. The product obtained is washed in the cold with 10% alkali and precipitated with allyl-amide salicylacetic acid with dilute hydrochloric or sulfuric acid, sucked off, washed with water and recrystallized from alcohol. A product is obtained with a m.p. 120-121 °.
Предмет изобретени ..The subject invention ..
Способ получени аллиламидса/ иаилуксусной кислоты отличающийс тем, что этиловый эфир амидсалицилуксусной кислоты Е|заимодействием с металлическим натрием в нейтральных органических растворител х как бензол и его гомологи , перевод т в его натриевое соедин ние , после чего обрабатывают бромистым аллилом и полученный; продукт, омыл ют на холоду.The method of producing allyl amide / i-acetic acid in which ethyl amide salicylacetic acid ester E | is borrowed with metallic sodium in neutral organic solvents such as benzene and its homologs, is converted into its sodium compound, and then treated with allyl bromide and the resulting; the product is washed cold.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SU123802A SU31437A1 (en) | 1933-02-13 | 1933-02-13 | The method of obtaining allylamine salicylacetic acid |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SU123802A SU31437A1 (en) | 1933-02-13 | 1933-02-13 | The method of obtaining allylamine salicylacetic acid |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU31437A1 true SU31437A1 (en) | 1933-08-31 |
Family
ID=48348757
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU123802A SU31437A1 (en) | 1933-02-13 | 1933-02-13 | The method of obtaining allylamine salicylacetic acid |
Country Status (1)
| Country | Link |
|---|---|
| SU (1) | SU31437A1 (en) |
-
1933
- 1933-02-13 SU SU123802A patent/SU31437A1/en active
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