SU311902A1 - METHOD OF OBTAINING FLUORINUM DERIVATIVES OF ORGANIC COMPOUNDS - Google Patents
METHOD OF OBTAINING FLUORINUM DERIVATIVES OF ORGANIC COMPOUNDSInfo
- Publication number
- SU311902A1 SU311902A1 SU1393542A SU1393542A SU311902A1 SU 311902 A1 SU311902 A1 SU 311902A1 SU 1393542 A SU1393542 A SU 1393542A SU 1393542 A SU1393542 A SU 1393542A SU 311902 A1 SU311902 A1 SU 311902A1
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- organic compounds
- derivatives
- fluorinum
- obtaining
- sodium
- Prior art date
Links
- 150000002894 organic compounds Chemical class 0.000 title description 8
- WEVYAHXRMPXWCK-UHFFFAOYSA-N acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N methylene dichloride Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- KEAYESYHFKHZAL-UHFFFAOYSA-N sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 2
- 238000005796 dehydrofluorination reaction Methods 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 230000003993 interaction Effects 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L mgso4 Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 150000003385 sodium Chemical class 0.000 description 2
- IYXGSMUGOJNHAZ-UHFFFAOYSA-N Diethyl malonate Chemical compound CCOC(=O)CC(=O)OCC IYXGSMUGOJNHAZ-UHFFFAOYSA-N 0.000 description 1
- UQSQSQZYBQSBJZ-UHFFFAOYSA-M Fluorosulfonate Chemical compound [O-]S(F)(=O)=O UQSQSQZYBQSBJZ-UHFFFAOYSA-M 0.000 description 1
- 238000007792 addition Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- -1 difluoroamino Chemical group 0.000 description 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 150000004812 organic fluorine compounds Chemical class 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002194 synthesizing Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Description
Изобретение Относитс к области химии фторорганических соединений.The invention relates to the field of organofluorine chemistry.
Полученные по предлагаемому способу фториминопроизБОДные органических соединений в литературе не описаны. Они обладают физиологической активностью и могут найти применение в качестве мономеров дл полимеризации и сополимеризации с непредельными соедннени ми.Obtained by the proposed method, fluorine-reproducible organic compounds are not described in the literature. They have physiological activity and can be used as monomers for polymerization and copolymerization with unsaturated compounds.
Известен способ получени фториминопроизводных органических соединений, основанный на взаимодействии непредельных органических соединений с тетр афторгидразином с последующим дегидрофторированием образующихс бис (дифторамино) производных.A known method for the preparation of fluorimino derivatives of organic compounds is based on the interaction of unsaturated organic compounds with tetra aftorgidrazine, followed by dehydrofluorination of the resulting bis (difluoroamino) derivatives.
Предлагаемый способ в отличие от известного позвол ет получать соединени , содержащие одну NF-rpynny, и избежать стадию дегидрофторировани .The proposed method, in contrast to the known method, makes it possible to obtain compounds containing one NF-rpynny and to avoid the dehydrofluorination stage.
Способ получени фториминопроизводных органических соединений основан на взаимодействии оксидифтораминофторсульфоната с натриевым .производным органических соединений , например натрмалоновым эфиром, в среде ацетонитрила при пониженной температуре .The method of producing fluorimino derivatives of organic compounds is based on the interaction of oxydifluoroaminofluorosulfonate with a sodium derivative of organic compounds, for example, sodium methyl ether, in an acetonitrile medium at a lower temperature.
спензию 0,025 моль натрмалонового эфира (полученного из 0,56 г натри и 4 г малонового эфира в 25 мл абсолютированного метилового спирта с последующим упариваниемSponge of 0.025 mol of natrmalonic ester (obtained from 0.56 g of sodium and 4 g of malonic ester in 25 ml of absolute methyl alcohol, followed by evaporation
смеси досуха в вакууме) в 30 мл ацетонитрила (синтез проводитс -в атмосфере азота). По окончании прибавлени суспензии охлаждение снимают, смесь выдерживают при перемешивании и постепенном повышении температуры до комнатной около 30 мин, продувают азотом и выливают в лед ную воду. Выпавшее масло отдел ют, воду экстрагируют два раза по 25 мл хлористым метиленом , после чего хлористый метилен и маслоmixture to dryness under vacuum) in 30 ml of acetonitrile (the synthesis is carried out under nitrogen). Upon completion of the addition of the suspension, the cooling is removed, the mixture is kept under stirring and the temperature is gradually raised to room temperature for about 30 minutes, purged with nitrogen and poured into ice water. The precipitated oil is separated, water is extracted twice with 25 ml of methylene chloride, followed by methylene chloride and oil
объедин ют и еще раз промывают лед ной водой. Экстракт сушат сернокислым магнием, упаривают в вакууме и фракционированием получают 1,4 г (29,3%) бесцветной жидкости с т. кип. 65°С/1 мм, п 1,4130 - фториминодиэтилмалоновый эфир.combined and again washed with ice water. The extract is dried with magnesium sulphate, evaporated in a vacuum and 1.4 g (29.3%) of a colorless liquid are obtained by fractionation with a boil. 65 ° С / 1 mm, p 1.4130 - fluorimino diethyl malonic ether.
Найдено, %: F 10,11; .N 7,49; С 43,61; Н 5,43.Found,%: F 10.11; .N 7.49; C 43.61; H 5.43.
C7HioF NO4.C7HioF NO4.
Вычислено, %: F 9,95; N 7,33; С 43,98; Н 5,23. 3 Аналогично получен фториминодинитрил малоновой кислоты с т. кип. 66°С, п 1,4092. Предмет изооретени 1. Способ получени фториминопроизвод-5 ных органических соединений общей формулы (R)2 - C NF, Где R - СООС2Н5, CN, отличающийс тем, что оксидифторамино4 фторсульфонат подвергают взаимодействию с натриевым производным органически.ч соединений , например натрмалоновым эфиром, при пониженной температуре с последующим выделением целевого .продукта -известным способом . 2. Способ по п. 1, отличающийс тем, что процесс провод т в среде ацетонитрила.Calculated,%: F 9.95; N 7.33; C 43.98; H 5.23. 3 Similarly, fluorinimine nitrile of malonic acid was obtained with m. Bale. 66 ° C, p 1.4092. Subject of ioretration 1. A method of producing fluorimino derivatives of organic compounds of general formula (R) 2 - C NF, where R is COOC2H5, CN, characterized in that the oxydifluoroamine fluorosulfonate is reacted with a sodium derivative of organic compounds, for example, sodium ether, with low temperature followed by isolation of the target product in a known manner. 2. A method according to claim 1, characterized in that the process is carried out in an acetonitrile medium.
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU311902A1 true SU311902A1 (en) |
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