SU366711A1 - Method for preparing 0-aryl esters of substituted thiocarbamic acid - Google Patents
Method for preparing 0-aryl esters of substituted thiocarbamic acidInfo
- Publication number
- SU366711A1 SU366711A1 SU1617692A SU1617692A SU366711A1 SU 366711 A1 SU366711 A1 SU 366711A1 SU 1617692 A SU1617692 A SU 1617692A SU 1617692 A SU1617692 A SU 1617692A SU 366711 A1 SU366711 A1 SU 366711A1
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- aryl esters
- thiocarbamic acid
- preparing
- substituted thiocarbamic
- acid
- Prior art date
Links
- 238000000034 method Methods 0.000 title description 8
- 150000003560 thiocarbamic acids Chemical class 0.000 title description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- -1 aryl isothiocyanates Chemical class 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- ITAMCOCNZJPJDF-UHFFFAOYSA-N 1-(6-aminopurin-9-yl)propan-2-yloxymethyl-phenoxyphosphinic acid Chemical compound C1=NC2=C(N)N=CN=C2N1CC(C)OCP(O)(=O)OC1=CC=CC=C1 ITAMCOCNZJPJDF-UHFFFAOYSA-N 0.000 description 1
- SNLGBRZZFRSXHA-UHFFFAOYSA-N 1-iodo-4-isothiocyanatobenzene Chemical compound IC1=CC=C(N=C=S)C=C1 SNLGBRZZFRSXHA-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- MMCPOSDMTGQNKG-UHFFFAOYSA-N anilinium chloride Chemical compound Cl.NC1=CC=CC=C1 MMCPOSDMTGQNKG-UHFFFAOYSA-N 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- 150000001989 diazonium salts Chemical class 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 150000002540 isothiocyanates Chemical class 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
1one
Изобретение относитс к способам получени О-ариловых эфиров замещенной тиокарбаминовой кислоты, которые обладают физиологической активностью, а также могут вл тьс промежуточными продуктами дл синтеза различных типов органических соединений .The invention relates to methods for producing O-aryl esters of substituted thiocarbamic acid, which have physiological activity and may also be intermediate products for the synthesis of various types of organic compounds.
Известен способ синтеза О-ариловых эфиров замещенной тиокарбаминовой кислоты путем взаимодействи ариламинов с хлорангидридом монофенилового эфира тиоугольной кислоты.A known method for synthesizing O-aryl esters of substituted thiocarbamic acid by reacting arylamines with the chlorohydride of a mono-phenyl ester of triangular acid.
Однако способ многостадиен и дл осуществлени его приходитс использовать труднодоступное сырье.However, the method is multistage and it is necessary to use hard-to-reach raw materials to carry it out.
Предлагаетс арилизотиоцианаты подвергать взаимодействию с сол ми арилдиазони в щелочной среде при комнатной темлературе или при нагревании до 40-бОС. Целевой продукт выдел ют известным способом. При этом получаютс симметричные и несиммет2It is proposed that aryl isothiocyanates be reacted with aryldiazonium salts in alkaline medium at room temperature or when heated to 40 bOS. The desired product is isolated in a known manner. Symmetric and unbalanced are obtained.
ричные О-ариловые эфиры замещенной тиокарбаминовой кислоты с выходом 60-80%.tricky O-aryl esters of substituted thiocarbamic acid with a yield of 60-80%.
Пример. О-Фениловый эфир п-йодфенилтиокарбаминовой кислоты.Example. O-phenyl ester of p-iodophenylthiocarbamic acid.
1,86 г (0,02 моль) анилина суспендируют в 0,6 мл сол ной кислоты (уд. в. 1,19) и 1 мл воды. Полученную сол нокислую соль анилина диазотируют 1,38 г (0,02 моль) нитрита натри , растворенного в 2 мл воды, при О-1.86 g (0.02 mol) of aniline are suspended in 0.6 ml of hydrochloric acid (sp. 1.19) and 1 ml of water. The resulting aniline hydrochloride salt diazotizes 1.38 g (0.02 mol) of sodium nitrite dissolved in 2 ml of water at O—
5°С. Полученный раствор соли диазони прибавл ют постепенно к 5,24 г (0,02 моль) пйодфенилизотиоцианата , растворенного в водно-спиртовой щелочи (0,8 г едкого натра, 1,2 мл спирта и 2 мл воды). Реакционную5 ° C. The resulting solution of the diazonium salt is gradually added to 5.24 g (0.02 mol) of pyrophenyl isothiocyanate dissolved in hydroalcoholic alkali (0.8 g of sodium hydroxide, 1.2 ml of alcohol and 2 ml of water). Reactionary
смесь нагревают до 50°С при перемешивании в течение 3-5 мин. Выпадает коричневый осадок. После перекристаллизации из спирта выход 4,84 г (80%, счита на п-йодфенилизотиоцианат ).the mixture is heated to 50 ° C with stirring for 3-5 minutes. Brown precipitate falls out. After recrystallization from alcohol, yield 4.84 g (80%, calculated as p-iodophenyl isothiocyanate).
Приведенные в таблице соединени получают аналогично. Найдено. %: С 67,77; 67,79; Н 4,97; 5, Вычислено, %: С 68,12; Н 4,8. Предмет изобретени 1. Способ получени О-ариловых эфиров замещенной тиокарбаминовой кислоты, отличающийс тем, что арилизотиоцианаты подвергают взаимодействию с сол ми арилдиазопи в щелочной среде с последующим выделением целевого продукта известными приемами . 2. Способ по п. 1, отличающийс тем, что процесс провод т при 20-50°С.The compounds listed in the table are prepared similarly. Found %: C, 67.77; 67.79; H 4.97; 5, Calculated,%: C 68.12; H 4.8. The subject matter of the invention is 1. A method for the preparation of O-aryl esters of substituted thiocarbamic acid, wherein the aryl isothiocyanates are reacted with aryl diazopy salts in an alkaline medium, followed by isolation of the target product by known techniques. 2. A method according to claim 1, characterized in that the process is carried out at 20-50 ° C.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SU1617692A SU366711A1 (en) | 1971-02-01 | 1971-02-01 | Method for preparing 0-aryl esters of substituted thiocarbamic acid |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SU1617692A SU366711A1 (en) | 1971-02-01 | 1971-02-01 | Method for preparing 0-aryl esters of substituted thiocarbamic acid |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU366711A1 true SU366711A1 (en) | 1975-02-25 |
Family
ID=20464983
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU1617692A SU366711A1 (en) | 1971-02-01 | 1971-02-01 | Method for preparing 0-aryl esters of substituted thiocarbamic acid |
Country Status (1)
| Country | Link |
|---|---|
| SU (1) | SU366711A1 (en) |
-
1971
- 1971-02-01 SU SU1617692A patent/SU366711A1/en active
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