SU299511A1 - METHOD FOR PREPARING AMMONIUM SALTS OF AMIDES RALKOXIVINYLPHOSPHONE ACIDS - Google Patents
METHOD FOR PREPARING AMMONIUM SALTS OF AMIDES RALKOXIVINYLPHOSPHONE ACIDSInfo
- Publication number
- SU299511A1 SU299511A1 SU1396941A SU1396941A SU299511A1 SU 299511 A1 SU299511 A1 SU 299511A1 SU 1396941 A SU1396941 A SU 1396941A SU 1396941 A SU1396941 A SU 1396941A SU 299511 A1 SU299511 A1 SU 299511A1
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- amides
- acids
- ammonium salts
- ralkoxivinylphosphone
- preparing ammonium
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 12
- 239000002253 acid Substances 0.000 title claims description 8
- 150000001408 amides Chemical class 0.000 title claims description 7
- 150000003863 ammonium salts Chemical class 0.000 title claims description 7
- 150000007513 acids Chemical class 0.000 title claims description 4
- 150000001412 amines Chemical class 0.000 claims description 3
- 238000002955 isolation Methods 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 150000003335 secondary amines Chemical class 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 claims 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical compound CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 description 5
- UHBGYFCCKRAEHA-UHFFFAOYSA-N P-toluamide Chemical compound CC1=CC=C(C(N)=O)C=C1 UHBGYFCCKRAEHA-UHFFFAOYSA-N 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 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
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methyl-N-phenylamine Natural products CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 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
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000008139 complexing agent Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- XQRLCLUYWUNEEH-UHFFFAOYSA-N diphosphonic acid Chemical compound OP(=O)OP(O)=O XQRLCLUYWUNEEH-UHFFFAOYSA-N 0.000 description 1
- 229940042400 direct acting antivirals phosphonic acid derivative Drugs 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 150000003007 phosphonic acid derivatives Chemical class 0.000 description 1
- -1 pyrophosphonic acid p-tolylammonium salt Chemical class 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
Description
Изобретение относитс к способу получени производных фосфоновых кислот.The invention relates to a process for the preparation of phosphonic acid derivatives.
Предлагаетс новый способ получени аммониевых солей амидов р-алкоксивинилфосфоновых кислот общей формулыA new method is proposed for the preparation of ammonium salts of p-alkoxyvinylphosphonic acid amides of the general formula
RR
/Nx -р / Nx - p
CH ::CHII OH .N,,CH :: CHII OH .N ,,
гдеR - алкил;where R is alkyl;
R и R - водород или R and R is hydrogen or
углеводородный радикал.hydrocarbon radical.
Предлагаемый способ основан на известном способе получени аммониевых солей амидов пирофосфоновых кислот с аминами при нагревании . Однако аммониевые соли амидов ралкоксивинилфосфоновых кислот в литературе не описаны. Они могут найти применение в качестве комплексообразователей, а также полупродуктов синтеза высокомолекул рных соединений и пестицидов.The proposed method is based on the well-known method of producing ammonium salts of amides of pyrophosphonic acids with amines when heated. However, the ammonium salts of the amides of ralkoxyvinylphosphonic acids are not described in the literature. They can be used as complexing agents, as well as intermediates for the synthesis of high molecular compounds and pesticides.
Способ заключаетс в том, что аммониевую соль амида р-алкоксивинилпирофосфоновой кислоты подвергают взаимодействию с первичным или вторичным амином с последующим выделением целевого продукта известнымиThe method consists in that the ammonium salt of the amide of p-alkoxyvinyl pyrophosphonic acid is reacted with a primary or secondary amine, followed by isolation of the target product with known
приемами. Процесс ведут при нагревании до 150-165°С в среде избыточного амина.tricks. The process is carried out when heated to 150-165 ° C in an environment of excess amine.
Пример 1. К 1,0 г (0,QQ2 г-моль) л-толиламмониевой соли п-толиламида р-этоксивинилпирофосфоновой кислоты прибавл ют 10-15кратный избыток п-толуидина и при перемещивании нагревают при 150-160°С в течение 5-6 час. Смесь промывают абсолютным эфиром , сушат в вакуум-эксикаторе и получаютExample 1. To 1.0 g (0, QQ2 g-mol) of p-tolylamide p-ethoxyvinyl pyrophosphonic acid p-tolylammonium salt of l-tolyl ammonium salt is added 10-15 fold excess of p-toluidine and while being heated it is heated at 150-160 ° C for 5 6 o'clock The mixture is washed with absolute ether, dried in a vacuum desiccator and get
1,2 г (выход 83%) л-толиламмониевой соли rt-толиламида р-этоксивинилфосфоновой кислоты , хорошо растворимой в воде, спирте и не растворимой в бензоле, эфире, диоксане и хлороформе; т. пл. 90-92°С.1.2 g (83% yield) of lt-tolyl ammonium salt of rt-tolyl-amide p-ethoxy vinylphosphonic acid, soluble in water, alcohol, and insoluble in benzene, ether, dioxane, and chloroform; m.p. 90-92 ° C.
Найдено, %: N 7,61; 7,72; Р 9,53; 9,42. CisHzsOsNaP.Found,%: N 7.61; 7.72; P 9.53; 9.42. CisHzsOsNaP.
Вычислено, %: N 8,0; Р 8,9. Пример 2. К 2,0 г (0,0037 г-моль) п-толиламмониевой соли п-толиламида р-пропокси-а-метилвинилпирофосфоновой кислоты прибавл ют 10-15-кратный избыток л-толуидина и при перемешивании нагревают при 160- 165°С в течение 5-6 час. Смесь промывают абсолютным эфиром, сушат в вакуум-эксикаторе и получают 2,12 г (выход 76%) л-толиламмониевой соли и-толиламида р-пропоксиа-метилвинилфосфоновой кислоты, хорошо растворимой в воде, спирте, ацетоне и не растворимой в бензоле, эфире, диоксане; т. пл.Calculated,%: N 8.0; R 8.9. Example 2. To a 2.0 g (0.0037 g-mol) p-tolylammonium salt of p-tropylamide p-propoxy-a-methylvinylpyrophosphonic acid p-tolylamide was added 10-15 fold excess of p-toluidine and heated at 160-165 with stirring ° C for 5-6 hours. The mixture is washed with absolute ether, dried in a vacuum desiccator and get 2.12 g (yield 76%) of p-propoxy-methylvinylphosphonic acid p-propoxy-methylvinylphosphonic acid l-tolylammonium salt and soluble in water, alcohol, acetone and insoluble in benzene, ether dioxane; m.p.
Найдено, %: N 7,28; 7,33; Р 8,94; 8,77.Found,%: N 7.28; 7.33; P 8.94; 8.77.
СгоНгзОзЫгР.SgoNGZOZYR.
Вычислено, %: N 7,4; Р 8,2.Calculated,%: N 7.4; P 8.2.
Предмет изобретени Subject invention
Claims (3)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU299511A1 true SU299511A1 (en) |
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