SU368235A1 - [PDTNII ^ 'G'CH-y! - Google Patents
[PDTNII ^ 'G'CH-y!Info
- Publication number
- SU368235A1 SU368235A1 SU1439083A SU1439083A SU368235A1 SU 368235 A1 SU368235 A1 SU 368235A1 SU 1439083 A SU1439083 A SU 1439083A SU 1439083 A SU1439083 A SU 1439083A SU 368235 A1 SU368235 A1 SU 368235A1
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- chloroethyl
- heated
- mixture
- thionyl chloride
- pdtnii
- Prior art date
Links
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 8
- -1 aliphatic nitramine derivatives Chemical class 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000011592 zinc chloride Substances 0.000 description 2
- 235000005074 zinc chloride Nutrition 0.000 description 2
- POCJOGNVFHPZNS-ZJUUUORDSA-N (6S,7R)-2-azaspiro[5.5]undecan-7-ol Chemical compound O[C@@H]1CCCC[C@]11CNCCC1 POCJOGNVFHPZNS-ZJUUUORDSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 241000289669 Erinaceus europaeus Species 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- BSPUVYFGURDFHE-UHFFFAOYSA-N Nitramine Natural products CC1C(O)CCC2CCCNC12 BSPUVYFGURDFHE-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- MFSIEROJJKUHBQ-UHFFFAOYSA-N O.[Cl] Chemical class O.[Cl] MFSIEROJJKUHBQ-UHFFFAOYSA-N 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- POCJOGNVFHPZNS-UHFFFAOYSA-N isonitramine Natural products OC1CCCCC11CNCCC1 POCJOGNVFHPZNS-UHFFFAOYSA-N 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Изобретение относитс к синтезу N- (2-хлорэтил )-М-алкилнитра.мИНОв, кото1рые могут быть использованы как биологически активные соединени или как исходные продукты дл получени производных алифатических нитраминов.The invention relates to the synthesis of N- (2-chloroethyl) -M-alkylnitra. Aniline, which can be used as biologically active compounds or as starting materials for the preparation of aliphatic nitramine derivatives.
Известен способ получени М-(2-хлорэтил)N-алкилнитрамина путем обработки хлоргидрата Ы-(2-хлорэтил)-|М-алкиламина концентрированной азотной кислотой с последующей дегидратацией азотнокислой соли амина уксусйым ангидридом.A known method for producing M- (2-chloroethyl) N-alkylnitramine by treating N- (2-chloroethyl) - | M-alkylamine hydrochloride with concentrated nitric acid followed by dehydration of the nitrate amine salt with acetic anhydride.
Недостатком известного способа вл етс использование высокотоксичных хлоргидратов Ы-(2-хлорэтил)-;Н-алкиламинов или азотистых ипритов.The disadvantage of this method is the use of highly toxic chlorine hydrates L- (2-chloroethyl) -; N-alkylamines or nitrogen mustards.
С целью упрощени процесса предлагаетс N- (2 - нитрооксиэтил) -N-алкилнитрамины нагревать с тионилхлоридом в присутствии минеральных ИЛИ апротонных кислот. Желательно вести процесс при 50-80°С. Получаемые с высоким выходом Ы-(2-хлорэтил)-1Ч-алкилнитрамипы имеют высокую степень чистоты и стабильные характеристики.In order to simplify the process, N- (2-nitrooxyethyl) -N-alkyl nitramines are proposed to be heated with thionyl chloride in the presence of mineral OR aprotic acids. It is desirable to conduct the process at 50-80 ° C. The yielded, high-yield yl (2-chloroethyl) -1p-alkyl nitraps have a high degree of purity and stable characteristics.
Пример 1. Получениеди-(р-хлорэтил)нитрамина .Example 1. Obtaining uni- (p-chloroethyl) nitramine.
Смесь 9,6 г (0,05 моль}ди-(р-нитрооксиэтил )-нитрами1на, 95,2 г (0,8люль)тиоиплхлорида и 13,63 г хлористого цин1ка выдерживают 1 час при 39-35°С, затем постепенно в течение 6-8 час нагревают до температуры кипени чистого тионилхлорида (79С). Пзбыток тионилхлорида отгон ют, остаток сливают в холодную воду, экстрагируют эфиром, промывают 2%-ным содовым раствором до щev oчпoй реакции и сушат над сульфатом магни . Растворитель упаривают, остатокA mixture of 9.6 g (0.05 mol} of di- (p-nitrooxyethyl) -nitrami, 95.2 g (0.8%) of thioyl chloride and 13.63 g of zinc chloride is kept for 1 hour at 39-35 ° C, then gradually within 6-8 hours, the mixture is heated to the boiling point of pure thionyl chloride (79 ° C). The excess of thionyl chloride is distilled off, the residue is poured into cold water, extracted with ether, washed with a 2% soda solution to dry the mixture and dried over magnesium sulfate. The solvent is evaporated the remainder
фракционируют в вакууме (1 лм( рт. сг.) и получают 6 г (80%) целевого продукта. Т. кип. 97°С/1 ,ииг; л о 1,5132; d 1,4137.fractionated in vacuo (1 lm (Hg. sg.) and get 6 g (80%) of the target product. So Kip. 97 ° C / 1, ig; l about 1,5132; d 1,4137.
Найдено, %: С 26,28; 26,06; Н 4,27; 4,65; :N 14,18; 14,19; 39,60.Found,%: C 26.28; 26.06; H 4.27; 4.65; : N 14.18; 14.19; 39.60.
C4H8N802C12.C4H8N802C12.
Вычислено, %: С 25,66; Н 4,54; N 14,87; 39,95.Calculated,%: C 25.66; H 4.54; N 14.87; 39.95.
В ИК - спектре обнаружены полосы полощени при 640 (), 1540 и 1280 (NNOs) . Полоса поглощени при 1640In the IR spectrum, peeling bands are detected at 640 (), 1540, and 1280 (NNOs). Absorption band at 1640
(ON02) отсутствует.(ON02) is missing.
Пример 2. Получение Example 2. Getting
2-хлорэтил метил«итрамива .2-chloroethyl methyl "iramiva.
Смесь 33 г (0,2 моль) 2-нитрооксиэтнлметнлнитрамина , 238 г (2 моль) тионилхлорида и 6,5 г хлористого цинка выдерживают 1 час при 35-40°С, затем в течение 4 час нагревают до 79°С и выдел ют продукт, как в примере 1. Выход 21 г (76%). Т. кил. 71°С/1 лгж; 1,4930; d1 1,3057. Найдено, %: С 25,52; 25,70; Н 5,30; 5,81; N 19,98; 20,32; 30,51. СзНэЫгОзС. Вычислено, %: С 25,63; Н 5,77; N 20,21; 30,47. В ИК-спектре обнаружены полосы погло650 (С - С1), 1530 и 1300 щени при (NNOs) еж-. Предмет изобретени 1. Способ получени К-(2-хлорэтил)-Ы-алкилнитраминов , отличающийс тем, что, с целью yrtjpidliteHMH Процесса, Ы-(2-нитрооксиэтил )-Ы-алкилн1Итрам«ны обрабатывают тионилхлоридом в присутствии сйльиых минеральных ИЛИ апротонных кислот при нагревании . 2. Способ пол. 1. отличающийс тем, что процесс провод т при .A mixture of 33 g (0.2 mol) of 2-nitrooxyethylmethylnitramine, 238 g (2 mol) of thionyl chloride and 6.5 g of zinc chloride is kept for 1 hour at 35-40 ° C, then heated for 4 hours to 79 ° C and separated product as in example 1. Yield 21 g (76%). T. Kil. 71 ° С / 1 лгж; 1.4930; d1 1.3057. Found,%: C 25.52; 25.70; H 5.30; 5.81; N 19.98; 20.32; 30.51. SzNeYgOzS. Calculated,%: C 25.63; H 5.77; N 20.21; 30.47. In the IR spectrum, bands of absorbed 650 (C – C1), 1530 and 1300 puffs were detected with (NNOs) hedgehog. The subject matter of the invention is 1. A method for producing K- (2-chloroethyl) -Y-alkylnitramines, characterized in that, for the purpose of the yrtjpidliteHMH Process, N- (2-nitrooxyethyl) -Y-alkyl1. when heated. 2. The way the floor. 1. characterized in that the process is carried out at.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SU1439083A SU368235A1 (en) | 1970-05-27 | 1970-05-27 | [PDTNII ^ 'G'CH-y! |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SU1439083A SU368235A1 (en) | 1970-05-27 | 1970-05-27 | [PDTNII ^ 'G'CH-y! |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU368235A1 true SU368235A1 (en) | 1973-01-26 |
Family
ID=20453023
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU1439083A SU368235A1 (en) | 1970-05-27 | 1970-05-27 | [PDTNII ^ 'G'CH-y! |
Country Status (1)
| Country | Link |
|---|---|
| SU (1) | SU368235A1 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2378251C1 (en) * | 2008-09-26 | 2010-01-10 | Учреждение Российской академии наук Институт органической химии им. Н.Д. Зелинского РАН (ИОХ РАН) | Secondary nitramine synthesis method |
-
1970
- 1970-05-27 SU SU1439083A patent/SU368235A1/en active
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2378251C1 (en) * | 2008-09-26 | 2010-01-10 | Учреждение Российской академии наук Институт органической химии им. Н.Д. Зелинского РАН (ИОХ РАН) | Secondary nitramine synthesis method |
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