SU189852A1 - METHOD OF OBTAINING N-CARBEGOXYLKYLAMIDO-O-ARYL-METHYL THIOPHOSPHONATE - Google Patents
METHOD OF OBTAINING N-CARBEGOXYLKYLAMIDO-O-ARYL-METHYL THIOPHOSPHONATEInfo
- Publication number
- SU189852A1 SU189852A1 SU1046582A SU1046582A SU189852A1 SU 189852 A1 SU189852 A1 SU 189852A1 SU 1046582 A SU1046582 A SU 1046582A SU 1046582 A SU1046582 A SU 1046582A SU 189852 A1 SU189852 A1 SU 189852A1
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- carbegoxylkylamido
- aryl
- obtaining
- methyl thiophosphonate
- ether
- Prior art date
Links
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- YACKEPLHDIMKIO-UHFFFAOYSA-N Methylphosphonic acid Chemical class CP(O)(O)=O YACKEPLHDIMKIO-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Natural products OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 239000000370 acceptor Substances 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 239000004471 Glycine Substances 0.000 description 1
- IZUPBVBPLAPZRR-UHFFFAOYSA-N Pentachlorophenol Chemical compound OC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl IZUPBVBPLAPZRR-UHFFFAOYSA-N 0.000 description 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Substances CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 1
- -1 amino acid esters Chemical class 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 230000000269 nucleophilic Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000003247 radioactive fallout Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
Description
Предлагаетс способ получени не описанных ранее N-карбэтоксиалкнламидо-О-арилметилтиофосфонатов взаимодействием замещенных метилфосфоновых кислот с иуклеофильными агентами-фенолами или эфирами аминокислот (в зависимости от природы заместител ) в присутствии акцепторов хлористого водорода (триэтнламина) в среде инертного органического растворител .A method is proposed for the preparation of non-previously described N-carbethoxyalklamido-O-arylmethylthiophosphonates by reacting substituted methylphosphonic acids with nucleophilic phenols or amino acid esters (depending on the nature of the substituent) in the presence of hydrogen chloride acceptors (triethylamine) in an inert organic solvent.
Пример 1. К 3,2 г хлорангидрида О-2,4дихлорфенилметилтиофосфоновой кислоты в 30 мл хлороформа прибавл ют по капл м 2,55 г этилового эфира гликокол в 15 мл хлороформа при 2-4°С. Реакциоппую массу перемешивают 1 час при 2°С, 1 час при 10-20°С и 1 час при 30-35°С. Выпавший осадок хлоргидрата этилового эфира гликокол отфильтровывают . От фильтрата отгон ют растворитель , остаток перегон ют и получают N-кароэтоксиметиламидо - О-2,4-дихлорфенилтиофосфонат с т. кип. 178-180°С/0,32 мм, п 1,5600 и df 1,3737, MR ц найдено 80,848, вычислено 80,527.Example 1. To 3.2 g of o-2,4dichlorophenylmethylthiophosphonic acid chloride in 30 ml of chloroform was added dropwise 2.55 g of glycol ethyl ester in 15 ml of chloroform at 2-4 ° C. The reaction mass is stirred for 1 hour at 2 ° C, 1 hour at 10-20 ° C and 1 hour at 30-35 ° C. The precipitated hydrochloride ethyl ether glycine is filtered off. The solvent is distilled off from the filtrate, the residue is distilled and a N-caro-ethoxymethylamido-O-2,4-dichlorophenylthiophosphonate is obtained with an m.p. 178-180 ° C / 0.32 mm, p 1.5600 and df 1.3737, MR c found 80.848, calculated 80.527.
CiiHaiClaNOaPS.CiiHaiClaNOaPS.
Найдено, %: С 38,96; Н 4,45; Р 9,11; S 9,43.Found,%: C 38.96; H 4.45; P 9.11; S 9.43.
Вычислено, %: С 38,60; Н 4,12; Р 9,05; S 9,37.Calculated,%: C 38.60; H 4.12; P 9.05; S 9.37.
вой кислоты и 3 мл триэтиламина в 20 мл абсолютного эфира прибавл ют по капл м раствор 3,2 г пентахлорфепола в 10 мл абсолютного эфира при 6-9°С. Реакционную массу перемешивают 30 мин при 5°С и но 1 час при 10-15, 20 и 30°С, после чего оставл ют на 2 суток. Затем к смеси нриливают 50 мл холодной воды. В результате выпадают белые кристаллы. Далее в смесь ввод т эфир до растворени кристаллов и эфирный экстракт дважды промывают водой по 50 мл. После высушивани , отгонки эфира н перекристаллизации нз эфира н ацетона получают N-карбэтоксиметиламндо - О - пеитахлорфепнлметилтиофосфопат с выходом 39,4% и т. пл. 125,5 - 126°С.acid solution and 3 ml of triethylamine in 20 ml of absolute ether are added dropwise a solution of 3.2 g of pentachlorophenol in 10 ml of absolute ether at 6-9 ° C. The reaction mass is stirred for 30 minutes at 5 ° C and for 1 hour at 10-15, 20 and 30 ° C, after which it is left for 2 days. Then to the mixture poured 50 ml of cold water. As a result, white crystals fall out. Ether is then added to the mixture until the crystals dissolve and the ether extract is washed twice with 50 ml of water. After drying, distilling off the ether and recrystallizing it from the ester of n-acetone, N-carbethoxymethylamine-O-peitachlorophenylmethylthiophosphate is obtained in a yield of 39.4%, and the like. 125.5 - 126 ° C.
CmnnOsNClsPS.CmnnOsNClsPS.
Найдено, %: С1 39,49, 39,31; N 3,36, 3,43; S 6,81, 6,53.Found,%: C1 39.49, 39.31; N 3.36, 3.43; S 6.81, 6.53.
Вычислено, %: С1 39,79; N 3,14; S 7,19.Calculated,%: C1 39,79; N 3.14; S 7.19.
Предмет изобретени Subject invention
Снособ получени N-карбэтоксналкиламидоО-арилметилтиофосфонатов , отличающийс The process for the preparation of N-carbethoxnalkylamido O-arylmethylthiophosphonates, characterized by
тем, что заменденные метилфосфоновые кислоты подвергают взаимодействию с фенолами или эфирамн аминокислот в присутствии акцепторов хлористого водорода, панример триэтиламина , в среде инертного органическогоthat the substituted methylphosphonic acids are reacted with phenols or esters of amino acids in the presence of hydrogen chloride acceptors, triethylamine panrimer, in inert organic medium
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU189852A1 true SU189852A1 (en) |
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