SU321126A1 - METHOD OF OBTAINING SUBSTITUTED DIPHENYLPHOSPHINOIMINES - Google Patents
METHOD OF OBTAINING SUBSTITUTED DIPHENYLPHOSPHINOIMINESInfo
- Publication number
- SU321126A1 SU321126A1 SU1437154A SU1437154A SU321126A1 SU 321126 A1 SU321126 A1 SU 321126A1 SU 1437154 A SU1437154 A SU 1437154A SU 1437154 A SU1437154 A SU 1437154A SU 321126 A1 SU321126 A1 SU 321126A1
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- diphenylphosphinoimines
- carried out
- obtaining substituted
- substituted
- heated
- Prior art date
Links
- -1 sodium alkoxide Chemical class 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 3
- 150000002825 nitriles Chemical class 0.000 claims description 3
- YFPJFKYCVYXDJK-UHFFFAOYSA-N oxo(diphenyl)phosphanium Chemical compound C=1C=CC=CC=1[P+](=O)C1=CC=CC=C1 YFPJFKYCVYXDJK-UHFFFAOYSA-N 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 229910052708 sodium Inorganic materials 0.000 claims description 3
- 239000011734 sodium Substances 0.000 claims description 3
- 239000003054 catalyst Substances 0.000 claims description 2
- 241000566113 Branta sandvicensis Species 0.000 claims 1
- 101710038792 PALG1 Proteins 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- 238000010438 heat treatment Methods 0.000 claims 1
- 238000002955 isolation Methods 0.000 claims 1
- 150000001298 alcohols Chemical class 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000003708 ampul Substances 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 125000004435 hydrogen atoms Chemical group [H]* 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 150000002903 organophosphorus compounds Chemical class 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- SUSQOBVLVYHIEX-UHFFFAOYSA-N Benzyl cyanide Chemical compound N#CCC1=CC=CC=C1 SUSQOBVLVYHIEX-UHFFFAOYSA-N 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N Sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- ZIUSEGSNTOUIPT-UHFFFAOYSA-N ethyl 2-cyanoacetate Chemical compound CCOC(=O)CC#N ZIUSEGSNTOUIPT-UHFFFAOYSA-N 0.000 description 1
- PEDCQBHIVMGVHV-UHFFFAOYSA-N glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 239000008079 hexane Substances 0.000 description 1
- 230000000749 insecticidal Effects 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- XYFCBTPGUUZFHI-UHFFFAOYSA-N phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002194 synthesizing Effects 0.000 description 1
Description
Изобретение отИоситс к способам получени фосфорорганических соединений - фосфинов , а именно к новому способу получени неизвестных в литературе дифенилфосфиноиминов общей формулыThe invention of Iocite to methods for the preparation of organophosphorus compounds — phosphines, namely, to a new method for the preparation of diphenylphosphinoimines unknown in the literature of the general formula
(СбН5) -CI-bR,(CbH5) -CI-bR,
II i О NH где R - СООС2Н5 или СеНз.II i О NH where R is СООС2Н5 or СеНз.
В литературе известно присоедииение к нитрилам карбоновых кислот соединений, содержащих подвижный атом водорода, например спиртов.In the literature, the addition of nitriles of carboxylic acids to compounds containing a mobile hydrogen atom, such as alcohols, is known.
Предлагаемый способ получени дифенилфосфиноиминов путем присоединени фосфина , имеющего подвижный атом водорода, к нитрилам карбоновых кислот позвол ет получить новый, не описанный в литературе класс фосфорорганических соединений, которые могут найти примбнение в качестве полупродуктов элементоорганического синтеза дл получени инсектицидов и физиологически активных веществ.The proposed method for producing diphenylphosphinoimines by adding phosphine having a mobile hydrogen atom to nitriles of carboxylic acids makes it possible to obtain a new class of organophosphorus compounds not described in the literature, which can be found as intermediates for elemental synthesis for the production of insecticides and physiologically active substances.
ще до 1(Ю°С и в присутствии в качестве катализатора алкогол та натри .even up to 1 (10 ° C and in the presence of sodium alkylate as a catalyst.
Процесс ведут при п тикратном избытке нитрила карбоновой кислоты. Целевые ро .дукты выдел ют известными приемами.The process is carried out with a fivefold excess of carboxylic acid nitrile. The target products are isolated by known methods.
Пример 1. К 23,35 г этилового эфира циануксусНОЙ кислоты добавл ют 8 г окиси дифенилфосфина и несколько капель насыщенного спиртового раствора этилата натри .Example 1. To 23.35 g of cyanoacetic acid ethyl ester, 8 g of diphenylphosphine oxide and a few drops of a saturated alcohol solution of sodium ethoxide are added.
Реакционную смесь нагревают на глицериновой бане в запа нной ампуле при 100°С несколько часов. При охлаждении выпадают белые кристаллы, которые промывают на фильтре гексаном.The reaction mixture is heated on a glycerin bath in a sealed ampoule at 100 ° C for several hours. Upon cooling, white crystals precipitate, which are washed on the filter with hexane.
Получают 6,45 г (52%) карбэтоксиметил (дифенилфосфино)-имина. Т. пл. 176-178°С. Найдено, %: Р 9,87; N 4,51. Мол. вес 309. CnHisOsNP. Вычислено, %: Р 9,84; N 4,44. Мол. вес 315.6.45 g (52%) of carbethoxymethyl (diphenylphosphino) -imin is obtained. T. pl. 176-178 ° C. Found,%: P 9.87; N 4.51. Mol weight 309. CnHisOsNP. Calculated,%: P 9,84; N 4.44. Mol weight 315.
Строение полученного продукта подтверждено ИК-спектрами.The structure of the obtained product is confirmed by IR spectra.
П Р и М е Р 2. К 26 г цианистого бензила добавл ют 9 г окиси дифенилфоофина и несколько капель насыщенного спиртового раствораPRM and M e R 2. To 26 g of benzyl cyanide, add 9 g of diphenylphosphine oxide and a few drops of a saturated alcohol solution.
этилата натри . Реакционную смесь нагревают в запа нной ампуле при 100°С не сколько часов. Выпавшие кристаллы промывают на фильтре бензолом, затем эфиром. Получают 8,66 г (61%) бензол-(дифенилфосфино)-имиНайдено , %: Р 10,03; N 4,59. Мол. ве.с 307. CaoHisONP.ethylate sodium. The reaction mixture is heated in a sealed ampoule at 100 ° C for several hours. The precipitated crystals are washed on the filter with benzene, then with ether. 8.66 g (61%) of benzene- (diphenylphosphino) -imi were obtained. Found:%: P 10.03; N 4.59. Mol version 307. CaoHisONP.
Вычислено, %: Р 9,71; N 4,38. Мол. вес 319. Строение продукта подтверждено ИК-спектрами .Calculated,%: P 9,71; N 4.38. Mol weight 319. The structure of the product is confirmed by IR spectra.
Предмет изобретени Subject invention
Claims (3)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU321126A1 true SU321126A1 (en) |
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