SU345164A1 - METHOD OF OBTAINING TETRA- (l-NITROPHENYLIC) ETHER DICHLORMALOYLBISAMIDOPHOSPHORIC ACID - Google Patents
METHOD OF OBTAINING TETRA- (l-NITROPHENYLIC) ETHER DICHLORMALOYLBISAMIDOPHOSPHORIC ACIDInfo
- Publication number
- SU345164A1 SU345164A1 SU1263253A SU1263253A SU345164A1 SU 345164 A1 SU345164 A1 SU 345164A1 SU 1263253 A SU1263253 A SU 1263253A SU 1263253 A SU1263253 A SU 1263253A SU 345164 A1 SU345164 A1 SU 345164A1
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- acid
- ether
- nitrophenylic
- dichlormaloylbisamidophosphoric
- tetra
- Prior art date
Links
- 239000002253 acid Substances 0.000 title description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 title description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N phosphoric acid Substances OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 3
- -1 dichloromethyl bisamide phosphoric acid ester Chemical class 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 230000000855 fungicidal Effects 0.000 description 2
- 230000000749 insecticidal Effects 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- ZMANZCXQSJIPKH-UHFFFAOYSA-N triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 2
- KPZGRMZPZLOPBS-UHFFFAOYSA-N 1,3-dichloro-2,2-bis(chloromethyl)propane Chemical compound ClCC(CCl)(CCl)CCl KPZGRMZPZLOPBS-UHFFFAOYSA-N 0.000 description 1
- BTJIUGUIPKRLHP-UHFFFAOYSA-N 4-Nitrophenol Chemical compound OC1=CC=C([N+]([O-])=O)C=C1 BTJIUGUIPKRLHP-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- FTQWRYSLUYAIRQ-UHFFFAOYSA-N N-[(octadecanoylamino)methyl]octadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(=O)NCNC(=O)CCCCCCCCCCCCCCCCC FTQWRYSLUYAIRQ-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Natural products OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 230000002363 herbicidal Effects 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 150000003015 phosphoric acid halides Chemical class 0.000 description 1
- 239000011814 protection agent Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
Description
Изобретение относитс к получению амидоэфиров фосфорной кислоты, а именно к получению не описанного в литературе тетра (rt-нитрофенилового) -эфира дихлормалоилбисам идо фосфорной кислоты формулыThis invention relates to the preparation of phosphoric acid amido esters, namely, the preparation of the dichlorormaloylbis bis-phosphoric acid tetra (rt-nitrophenyl) ester not described in the literature.
-., .-.,.
CClJcONHPCClJcONHP
О ABOUT
Это соединение обладает высокой фунгицидной и инсектицидной активностью и может быть использовано как средство дл защиты растений.This compound has high fungicidal and insecticidal activity and can be used as a plant protection agent.
Известно, что диэфиры толигалоидациламидофосфорных кислот обладают гербицидной активностью. В отличие от них внервые синтезированный тетра-(/г - нитрофениловый)эфир дихлормалоилбисамидофосфорной кислоты имеет фунгицидные и инсектицидные свойства.It is known that diesters of toligloidacylamidophosphoric acids possess herbicidal activity. In contrast, the first-synthesized tetra - (/ g - nitrophenyl) dichloromethyl bisamide phosphoric acid ester has fungicidal and insecticidal properties.
Предлагаемый способ основан на известной реакции этерификации галоидангидридов фосфорной кислоты фенолами. Способ заключаетс в том, что тетрахлорангидрид дихлормалоилбисамидофосфорной квслоты подвергают взаимодействию с п-нитрофенолом.The proposed method is based on the known esterification reaction of phosphoric acid halides with phenols. The method consists in dichlorormaloyl bisamide phosphoric acid tetrachlorohydride which is reacted with p-nitrophenol.
Целевой продукт выдел ют известными приемами. Выход 62%.The desired product is isolated by known techniques. Yield 62%.
Пример. В круглодонную колбу емкостью 0,2 л помещают 0,04 г/моль л-нитрофенола , 0,04 г/моль триэтиламина, 0,04 г/моль тетрахлорангидрида дихлормалоилбисамидофосфорной кислоты в 20 мл бензола.Example. A 0.04 g / mol l-nitrophenol, 0.04 g / mol triethylamine, 0.04 g / mol dichloro-maloyl bisamidophosphoric acid tetrachloroanhydride in 20 ml of benzene was placed in a 0.2 l round-bottom flask.
Реакционную смесь кип т т 30-40 мин и оставл ют сто ть в течение 6 час при 20°С. Выделившуюс сол нокислую соль триэтиламина отсасывают. Бензол отгон ют в вакууме . В остатке - тетра-(п-нитрофбниловый)эфир дихлормалоиламидофосфорной кислоты в виде кристаллической массы, которую отсасьшают , сушат и кристаллизуют.The reaction mixture is boiled for 30-40 minutes and left to stand for 6 hours at 20 ° C. The released triethylamine hydrochloride salt is sucked off. The benzene is distilled off in vacuo. The residue contains tetra- (p-nitrofbnyl) dichloromeloyl-amidophosphoric acid ester as a crystalline mass, which is sucked off, dried and crystallized.
Выход 62%, т. пл. 107-108°С.Yield 62%, so pl. 107-108 ° C.
Вычислено, %: С1 9; N 10,60.Calculated,%: C1 9; N 10.60.
CarHisCUNeOiePa.CarHisCUNeOiePa.
Найдено, %: С1 8,94; N 10,10.Found,%: C1 8.94; N 10.10.
2020
Предмет изобретени Subject invention
Способ получени тетра-(«-нитрофенилового ) -эфира дихлормалоилбисамидофосфорнойThe method of obtaining the tetra - ("- nitrophenyl) -ether dichloromelobisamidophosphoric
кислоты, отличающийс тем, что тетрахлорангидрид дихлормалоилбисамидофосфорной кислоты подвергают взаимодействию с д-нитрофенолом в присутствии акцептора хлористого водорода в среде инертного органичеacid, characterized in that dichloromeloyl bisamidophosphoric acid tetrachloride is reacted with d-nitrophenol in the presence of hydrogen chloride acceptor in an inert organic medium
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU345164A1 true SU345164A1 (en) |
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