RU1841272C - The method of obtaining nitroadamantana - Google Patents
The method of obtaining nitroadamantana Download PDFInfo
- Publication number
- RU1841272C RU1841272C SU0001538363A SU1538363A RU1841272C RU 1841272 C RU1841272 C RU 1841272C SU 0001538363 A SU0001538363 A SU 0001538363A SU 1538363 A SU1538363 A SU 1538363A RU 1841272 C RU1841272 C RU 1841272C
- Authority
- RU
- Russia
- Prior art keywords
- nitroadamantane
- ozone
- adamantane
- nitroadamantana
- oxygen mixture
- Prior art date
Links
- HONLSNLUVRQMEK-UHFFFAOYSA-N 1-nitroadamantane Chemical compound C1C(C2)CC3CC2CC1([N+](=O)[O-])C3 HONLSNLUVRQMEK-UHFFFAOYSA-N 0.000 claims abstract description 7
- ORILYTVJVMAKLC-UHFFFAOYSA-N Adamantane Chemical class C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 claims abstract description 6
- 238000000034 method Methods 0.000 claims abstract description 5
- 239000000203 mixture Substances 0.000 claims abstract description 5
- YNHBOQSCVCFXRW-UHFFFAOYSA-N ozone;hydrate Chemical compound O.[O-][O+]=O YNHBOQSCVCFXRW-UHFFFAOYSA-N 0.000 claims abstract description 5
- 239000007800 oxidant agent Substances 0.000 claims abstract 3
- VBHCPGFCIQDXGZ-UHFFFAOYSA-N 1-isocyanatoadamantane Chemical compound C1C(C2)CC3CC2CC1(N=C=O)C3 VBHCPGFCIQDXGZ-UHFFFAOYSA-N 0.000 claims abstract 2
- 229940052761 dopaminergic Adamantane derivatives Drugs 0.000 claims abstract 2
- 239000003960 organic solvent Substances 0.000 claims abstract 2
- 238000000926 separation method Methods 0.000 claims 1
- 239000000126 substance Substances 0.000 abstract description 2
- 239000007795 chemical reaction product Substances 0.000 abstract 1
- 239000000047 product Substances 0.000 abstract 1
- IQPQWNKOIGAROB-UHFFFAOYSA-N [N-]=C=O Chemical compound [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 3
- DKNWSYNQZKUICI-UHFFFAOYSA-N Amantadine Chemical compound C1C(C2)CC3CC2CC1(N)C3 DKNWSYNQZKUICI-UHFFFAOYSA-N 0.000 description 2
- VZJVWSHVAAUDKD-UHFFFAOYSA-N Potassium permanganate Chemical compound [K+].[O-][Mn](=O)(=O)=O VZJVWSHVAAUDKD-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- CBENFWSGALASAD-UHFFFAOYSA-N ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 2
- ICVUAMUSASFFOR-REOHCLBHSA-N (2S)-2-nitramidopropanoic acid Chemical compound OC(=O)[C@H](C)N[N+]([O-])=O ICVUAMUSASFFOR-REOHCLBHSA-N 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- JIMXXGFJRDUSRO-UHFFFAOYSA-N adamantane-1-carboxylic acid Chemical compound C1C(C2)CC3CC2CC1(C(=O)O)C3 JIMXXGFJRDUSRO-UHFFFAOYSA-N 0.000 description 1
- 229910001573 adamantine Inorganic materials 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L cacl2 Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 238000006396 nitration reaction Methods 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 238000006385 ozonation reaction Methods 0.000 description 1
- 238000005020 pharmaceutical industry Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Abstract
Description
Настоящее изобретение относится к методам получения нитросоединений ациликлического ряда. Известно несколько способов получения нитроадамантана. Наиболее распространенными из них являются: нитрование адамантана азотной кислотой при температуре 140°С в автоклаве под давлением 40-50 атм и окисление аминоадамантана перманганатом калия с выходом нитроадамантана 71% и 30% соответственно.The present invention relates to methods for the production of nitro compounds of the acyliche series. There are several ways to get nitroadamantana. The most common of these are: nitration of adamantane with nitric acid at a temperature of 140 ° C in an autoclave under a pressure of 40-50 atm and oxidation of aminoadamantane with potassium permanganate with a yield of nitro admantane of 71% and 30%, respectively.
К недостаткам первого способа следует отнести использование специальной аппаратуры (автоклавы), высокую температуру и давление, а также опасность процесса.The disadvantages of the first method include the use of special equipment (autoclaves), high temperature and pressure, and the danger of the process.
К недостаткам же второго способа следует отнести низкий выход нитроадамантана и малую доступность исходного сырья (аминоадамантан получают из адамантанкарбоновой кислоты через изоцианат).The disadvantages of the second method include the low yield of nitroadamantane and the low availability of the starting material (aminoadamantane is obtained from adamantanecarboxylic acid via isocyanate).
Авторами разработан способ получения нитроадамантана окислением адамантилизоцианата озонокислородной смесью с концентрацией озона 10-12 об.% при атм. давлении и комнатной температуре в растворе хлорсодержащих углеводородов.The authors have developed a method for producing nitroadamantane by oxidation of adamant isocyanate by an ozone-oxygen mixture with an ozone concentration of 10–12% by volume at atm. pressure and room temperature in a solution of chlorine-containing hydrocarbons.
Способ прост и позволяет получить нитроадамантан с выходом 75%. Нитроадамантан может быть использован для получения полинитроадамантанов и аминоадамантана, который находит применение в фармацевтической промышленности.The method is simple and allows you to get nitroalanine with a yield of 75%. Nitroadamantane can be used to obtain polynitroadamantane and aminoadamantana, which finds application in the pharmaceutical industry.
Пример: Example:
Получение нитроадамантанаGetting nitroadamantana
Озонирование осуществляется в аппарате с барботером для пропускания озоно-кислородной смеси, обратным холодильником, термометром и механической мешалкой.Ozonation is carried out in the apparatus with a bubbler to pass the ozone-oxygen mixture, reflux condenser, thermometer and mechanical stirrer.
В раствор 17,7 г (0,1 моля) адамантинизоцианата в 500 мл сухого хлороформа при комнатной температуре и перемешивании пропускают озонокислородную смесь с концентрацией озона 10-12 об.% со скоростью 8-10 м/час в течение 10-12 час. Затем реакционную массу промывают три раза водой и сушат над безводным хлористым кальцием. После упаривания растворителя остаток сублимируют при температуре 85-90°/10-12 мм рт.ст. Выход 15,1 г (75% от теории), Т.пл. 158-159°С. Продукт хорошо кристаллизуется из метанола. Вещество идентифицировано как нитроадамантан.In a solution of 17.7 g (0.1 mol) of adamantine isocyanate in 500 ml of dry chloroform, an ozone-oxygen mixture with an ozone concentration of 10-12 vol.% At a speed of 8-10 m / h is passed through for 10-12 hours at room temperature with stirring. Then the reaction mass is washed three times with water and dried over anhydrous calcium chloride. After evaporation of the solvent, the residue is sublimated at a temperature of 85-90 ° / 10-12 mm Hg. Output 15.1 g (75% of theory), So pl. 158-159 ° C. The product crystallizes well from methanol. Substance identified as nitroadamantane.
Данные элементарного анализа:Elementary analysis data:
Найдено, в %: С 66,21; 65,90; 66,15; Н 8,40; 8,55; 8,60; N 7,75; 7,80; 7,69.Found in%: C 66.21; 65.90; 66.15; H 8.40; 8.55; 8.60; N 7.75; 7.80; 7,69.
Вычислено для C10H15NO2 в %: С 66,00, Н 8,5 N 7,7.Calculated for C 10 H 15 NO 2 in%: C 66.00, H 8.5 N 7.7.
Данные ИК-спектроскопии, в см-1: 800, 1370, 2860.The data of IR spectroscopy, in cm -1 : 800, 1370, 2860.
Нитроадамантан, полученный по предлагаемому способу, отличается высокой степенью чистоты.Nitroadamantane obtained by the proposed method, has a high degree of purity.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SU0001538363A RU1841272C (en) | 1971-08-04 | The method of obtaining nitroadamantana |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SU0001538363A RU1841272C (en) | 1971-08-04 | The method of obtaining nitroadamantana |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SU1841272A1 SU1841272A1 (en) | 2017-02-14 |
| RU1841272C true RU1841272C (en) | 2017-02-14 |
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