SU213814A1 - - Google Patents
Info
- Publication number
- SU213814A1 SU213814A1 SU1128529A SU1128529A SU213814A1 SU 213814 A1 SU213814 A1 SU 213814A1 SU 1128529 A SU1128529 A SU 1128529A SU 1128529 A SU1128529 A SU 1128529A SU 213814 A1 SU213814 A1 SU 213814A1
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- acid
- product
- compounds
- methylamide
- phenylthioacetic
- Prior art date
Links
- 238000000034 method Methods 0.000 description 6
- RMVRSNDYEFQCLF-UHFFFAOYSA-N phenyl mercaptan Natural products SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 4
- IXOFPUCWZCAFJX-UHFFFAOYSA-N 2-phenylethanethioic s-acid Chemical compound SC(=O)CC1=CC=CC=C1 IXOFPUCWZCAFJX-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- RNBPPDKWUJHCPW-UHFFFAOYSA-N 2-chloroacetate;methylazanium Chemical compound [NH3+]C.[O-]C(=O)CCl RNBPPDKWUJHCPW-UHFFFAOYSA-N 0.000 description 2
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 229910001628 calcium chloride Inorganic materials 0.000 description 2
- 239000001110 calcium chloride Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- DIJUOSYHQYABQM-UHFFFAOYSA-N 2-(2-ethylphenoxy)acetic acid Chemical compound CCC1=CC=CC=C1OCC(O)=O DIJUOSYHQYABQM-UHFFFAOYSA-N 0.000 description 1
- CEAXCCNKYPOHDP-UHFFFAOYSA-N 2-(2-fluorophenoxy)acetic acid Chemical compound OC(=O)COC1=CC=CC=C1F CEAXCCNKYPOHDP-UHFFFAOYSA-N 0.000 description 1
- FWEOQOXTVHGIFQ-UHFFFAOYSA-N 8-anilinonaphthalene-1-sulfonic acid Chemical compound C=12C(S(=O)(=O)O)=CC=CC2=CC=CC=1NC1=CC=CC=C1 FWEOQOXTVHGIFQ-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
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical class NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 1
- 229940106681 chloroacetic acid Drugs 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- MGJXBDMLVWIYOQ-UHFFFAOYSA-N methylazanide Chemical compound [NH-]C MGJXBDMLVWIYOQ-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
Description
СПОСОБ ПОЛУЧЕНИЯ N-МЕТИЛАМИДОВ ФЕНОКСИИЛИ ФЕНИЛТИОУКСУСНЫХ КИСЛОТMETHOD OF OBTAINING N-METHYLAMIDES PHENOXYLES OF PHENYL ACID ACID
Изобретение относитс к способу получени новых соединений общей формулыThis invention relates to a process for the preparation of new compounds of the general formula
-хСНаСОМНСНз-hSNaSOMNSNz
где R - Н, алкил, нитрогруппа или галоид, ,where R is H, alkyl, nitro or halogen,,
X - кислород или сера.X - oxygen or sulfur.
Предлагаемый способ получени соединений этого типа в литературе не описан.The proposed method for preparing compounds of this type is not described in the literature.
Соединени такой структуры могут быть использованы в сельском хоз йстве.Compounds of this structure can be used in agriculture.
Способ основан на реакции замещенных фенол тов и тиофенол тов щелочных металлов с N-метиламидом монохлоруксусной кислоты.The method is based on the reaction of substituted phenols and thiophenolates of alkali metals with N-methylamide monochloroacetic acid.
Реакцию провод т в водной среде или ереде органического растворител при умеренной температуре. Соединени представл ют собой кристаллические вещества.The reaction is carried out in an aqueous medium or pre-organic solvent at a moderate temperature. The compounds are crystalline substances.
Пример 1. Пол учение N-M е т и л а м ид а га-н итрофеноксиуксусной кисл о ты.Example 1. Gender teaching N-M et t and l and m id aa Mr itrophenoxy acetic acid.
хлоруксусной кислоты в 50 мл воды. Реакционную массу перемещивают при 60-70°С в течение 2,5-3 час, затем охлаждают комнатной температуры и экстрагируют продукт трем порци ми хлороформа по 50 мл. Сушат хлористым кальцием. После отгонки растворител получают продукт в виде светло-серых кристаллов, т. пл. 116-117°С (из спирта).chloroacetic acid in 50 ml of water. The reaction mass is transferred at 60-70 ° C for 2.5-3 hours, then cooled to room temperature and the product is extracted with three portions of chloroform 50 ml. Dried with calcium chloride. After distilling off the solvent, the product is obtained in the form of light gray crystals, mp. 116-117 ° C (from alcohol).
Аналогично получают N-метиламид лг-нитрофеноксиуксусной кислоты о-фторфеноксиуксусной кислоты, о-этилфеноксиуксусной кислоты .Similarly, N-methylamide of lg-nitrophenoxyacetic acid of o-fluorophenoxyacetic acid, o-ethylphenoxyacetic acid is obtained.
Пример 2. Получение N-M е т и л а м ида фенилтиоуксусной кислоты.Example 2. Preparation of N-M et and l and m of id of phenylthioacetic acid.
К раствору 13,2 г (0,1 моль} тиофенол та натри в 75 мл воды постепенно прибавл ют при перемещивании и 50-60°С водный раствор 10,8 г (0,01 моль} N-метилхлорацетамнда. Смесь выдерживают при этой температуре 2-3 час, затем охлаждают водой и продукт экстрагируют бензолом (трем порци ми по 75 мл}, сущат хлористым кальцием. После отгонки растворител получают продукт в виде светло-желтых кристаллов, т. пл. 87-8°С (из спирта).To a solution of 13.2 g (0.1 mol} thiophenol sodium in 75 ml of water is gradually added while moving and 50-60 ° C an aqueous solution of 10.8 g (0.01 mol} N-methylchloroacetamnd. The mixture is kept at this temperature for 2-3 hours, then cooled with water and the product is extracted with benzene (three 75 ml portions), calcium chloride. After the solvent is distilled off, the product is obtained as light yellow crystals, mp 87-8 ° C (from alcohol ).
Идентификаци полученных веществ произведена по результатам элементарного анализа .Identification of the substances produced by the results of elementary analysis.
N-метиламиды замещенных фенокси- и фенилтиоуксусных кислотN-methylamides of substituted phenoxy- and phenylthioacetic acids
Предмет изобретени Subject invention
Способ получени М-метиламидо.в феноксиили фенилтиоуксусных кислот общей формулыThe method of obtaining M-methylamido. In phenoxy or phenylthioacetic acids of the general formula
-xCH,CONHCH.-xCH, CONHCH.
где R - Н, алкил, нитрогруппа или галоид,where R is H, alkyl, nitro or halogen,
,,
X - кислород или сера,X - oxygen or sulfur,
отличающийс тем, что, с целью получени веществ, обладающих физиологически активными свойствами, фенол т или тиофенол тcharacterized in that, in order to obtain substances with physiologically active properties, phenol t or thiophenol
щелочного металла подвергают взаимодействию с N-метиламидом монохлоруксусной кислоты с последующим выделением целевых продуктов, обычными приемами.alkali metal is subjected to interaction with N-methylamide monochloracetic acid, followed by isolation of the target products, the usual methods.
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU213814A1 true SU213814A1 (en) |
Family
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4595409A (en) * | 1983-08-31 | 1986-06-17 | Sumitomo Chemical Company, Ltd. | Substituted phenyl-4,5,6,7-tetrahydro-2H-isoindole-1,3-diones, and their production and use |
| US4684397A (en) * | 1983-05-16 | 1987-08-04 | Sumitomo Chemical Company, Limited | 2-Substituted phenyl-4,5,6,7-tetrahydro-2H-iso-indole-1,3-diones, and their production and use |
| US4826533A (en) * | 1981-12-25 | 1989-05-02 | Sumitomo Chemical Company, Limited | N-(substituted phenyl)-tetrahydrophthalimide compounds, and their production and herbicide use |
| US4902832A (en) * | 1983-08-31 | 1990-02-20 | Sumitomo Chemical Company, Limited | 2-Substituted phenyl-4,5,6,7-tetrahydro-2H-isoindole-1,3-diones, and their production and use |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4826533A (en) * | 1981-12-25 | 1989-05-02 | Sumitomo Chemical Company, Limited | N-(substituted phenyl)-tetrahydrophthalimide compounds, and their production and herbicide use |
| US4938795A (en) * | 1981-12-25 | 1990-07-03 | Sumitomo Chemical Company, Limited | Tetrahydrophthalimide compounds, and their production and use |
| US4684397A (en) * | 1983-05-16 | 1987-08-04 | Sumitomo Chemical Company, Limited | 2-Substituted phenyl-4,5,6,7-tetrahydro-2H-iso-indole-1,3-diones, and their production and use |
| US4709049A (en) * | 1983-05-16 | 1987-11-24 | Sumitomo Chemical Company, Limited | 2-substituted phenyl-4,5,6,7,-tetrahydro-2H-indole-1,3,-diones, and their production and use |
| US4595409A (en) * | 1983-08-31 | 1986-06-17 | Sumitomo Chemical Company, Ltd. | Substituted phenyl-4,5,6,7-tetrahydro-2H-isoindole-1,3-diones, and their production and use |
| US4902832A (en) * | 1983-08-31 | 1990-02-20 | Sumitomo Chemical Company, Limited | 2-Substituted phenyl-4,5,6,7-tetrahydro-2H-isoindole-1,3-diones, and their production and use |
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