SU436817A1 - Method for preparing 2,4-dinitro-5-amino-1-x-benzene derivatives - Google Patents
Method for preparing 2,4-dinitro-5-amino-1-x-benzene derivativesInfo
- Publication number
- SU436817A1 SU436817A1 SU1767182A SU1767182A SU436817A1 SU 436817 A1 SU436817 A1 SU 436817A1 SU 1767182 A SU1767182 A SU 1767182A SU 1767182 A SU1767182 A SU 1767182A SU 436817 A1 SU436817 A1 SU 436817A1
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- dinitro
- amino
- preparing
- benzene derivatives
- derivatives
- Prior art date
Links
- 238000000034 method Methods 0.000 title description 5
- 150000001875 compounds Chemical class 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- WDCYWAQPCXBPJA-UHFFFAOYSA-N 1,3-dinitrobenzene Chemical class [O-][N+](=O)C1=CC=CC([N+]([O-])=O)=C1 WDCYWAQPCXBPJA-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- CQLUVMHXDVLHSK-UHFFFAOYSA-N 1-methylsulfanyl-2,4-dinitrobenzene Chemical compound CSC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O CQLUVMHXDVLHSK-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 150000005215 alkyl ethers Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- KAMGOKSXKBHPHL-UHFFFAOYSA-N benzene-1,2,3,4-tetramine Chemical compound NC1=CC=C(N)C(N)=C1N KAMGOKSXKBHPHL-UHFFFAOYSA-N 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 239000012210 heat-resistant fiber Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- IHUQJPKASFTOBM-UHFFFAOYSA-N n-(2,4-dinitrophenyl)hydroxylamine Chemical compound ONC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O IHUQJPKASFTOBM-UHFFFAOYSA-N 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
1one
Изобретение относитс к способу получени новых соединений 2,4-динитро-5-амино-1-Хпроизводных бензола, которые могут быть использованы в качестве сырь дл синтеза термостойких волокон.This invention relates to a process for the preparation of new compounds of 2,4-dinitro-5-amino-1-X-derivatives of benzene, which can be used as a raw material for the synthesis of heat-resistant fibers.
Известен способ получени 2,4-динитро-Замино-М-фенилгидроксиламина , заключающийс в том, что производные 2,4-динитробензола обрабатывают гидроксиламином и алкогол том щелочного металла в спиртовом растворе с последующим гидролизом образовавщегос комплексного соединени обычным способом и выделением целевого продукта в свободном виде известным способом.A method of producing 2,4-dinitro-Zamino-M-phenylhydroxylamine is known, which consists in that the 2,4-dinitrobenzene derivatives are treated with hydroxylamine and an alkali metal alcohol in an alcohol solution, followed by hydrolysis of the complex compound in the usual way and isolation of the target product in the free in a known manner.
Удалось установить, что при взаимодействии гидроксиламина с алкиловыми эфирамч 2,4-динитротиоанизола образуютс новые соеинени - 2,4-динитро-5-амино-1-х-Производных бензола, вл ющиес исходным сырьем дл синтеза термостойких полимерных материалов , содержащие в дре аминогруилу.It was possible to establish that the interaction of hydroxylamine with alkyl ether of 2,4-dinitrothioanisole produces new compounds, 2,4-dinitro-5-amino-1-x-benzene derivatives, which are the raw material for the synthesis of heat-resistant polymeric materials containing .
Предлагаемый способ заключаетс в том, что производные 2,4-динитро-1-х-бензолы, где X-SAr, SAIK, SCN, Аг-фенил, Alk-алкил обрабатывают в диоксане или диметилсульфоксиде гидроксиламином и алкогол том щелочного металла или гидроокиси щелочного металла в спирте с последующим разложением промежуточного соединени водой и выделением целевого продукта известными методами . Реакци проходит при комнатной температуре в течение 10-20 мин с выходом целевого продукта 80%, по следующей схеме:The proposed method consists in that the 2,4-dinitro-1-x-benzenes derivatives, where X-SAr, SAIK, SCN, Ag-phenyl, Alk-alkyl are treated in dioxane or dimethylsulfoxide with hydroxylamine and alkali metal alcohol or alkali hydroxide metal in alcohol, followed by decomposition of the intermediate with water and isolation of the target product by known methods. The reaction takes place at room temperature for 10-20 minutes with the yield of the target product 80%, according to the following scheme:
-NO.,-NO.,
С.гНг,оНS.gNg, OH
ОГ - КаХНОН Т N0,L Промежуточное соединение 1 раствор етс в воде с разложением, образу новые соединени 2,4-ди«итро-5-амино-1-х-бензолы.20 Использование в качестве «X серусодержащих заместителей приводит к получению вышеописанных продуктов (-применение других заместителей, например X-ОА1К, ОАг, приводит к продуктам другого типа замещени , в частности к 2,4-динитрофенилгидроксиламипу ). Это объ сн етс тем, что серусодержащие группы обладают более высокой нуклеофильпостью по сравнепию с алкокси- и арилоксигруппами , поэтому более подвержепным нуклеофнльной атаке- становитс атом углерода в положении 5 дра, где происходит замепхепие водорода на аминогруппу, а заместитель «X остаетс нетронутым. Таким образом, применение 2,4-динитро-1-Хбензолов (, SAIK, SCN, например. SCeHg, ЗСНз, SC2H5 и т. д.) позвол ет легко ввести аминогруппу в .положение 5 дра, что расшир ет возможности дл синтеза симметричного тетрааминобензола. Строение полученных соединений однозначпо доказано при помощи ЯМР-спектроокопии и элементного анализа. Резул-ьтаты анализа приведены в таблице.OG - KAHNON T N0, L Intermediate 1 dissolves in water with decomposition, forming new compounds 2,4-di "itro-5-amino-1-x-benzenes." 20 Using as X the sulfur-containing substituents results in the above products (-the use of other substituents, for example, X-OA1K, OAg, leads to products of another type of substitution, in particular to 2,4-dinitrophenylhydroxylamine). This is explained by the fact that sulfur-containing groups have a higher nucleophilicity compared to alkoxy and aryloxy groups, therefore the carbon atom in position 5 of the core, where the hydrogen substitutes for the amino group occurs, becomes more susceptible to nucleophilicity, and the substituent X remains untouched. Thus, the use of 2,4-dinitro-1-Hbenzenes (, SAIK, SCN, for example. SCeHg, ZSNz, SC2H5, etc.) makes it possible to easily introduce an amino group in the position of core 5, which expands the possibilities for the synthesis of symmetric tetraaminobenzene. The structure of the compounds obtained is unambiguously proved using NMR spectrocopy and elemental analysis. The results of the analysis are shown in the table.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SU1767182A SU436817A1 (en) | 1972-04-03 | 1972-04-03 | Method for preparing 2,4-dinitro-5-amino-1-x-benzene derivatives |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SU1767182A SU436817A1 (en) | 1972-04-03 | 1972-04-03 | Method for preparing 2,4-dinitro-5-amino-1-x-benzene derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU436817A1 true SU436817A1 (en) | 1974-07-25 |
Family
ID=20508936
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU1767182A SU436817A1 (en) | 1972-04-03 | 1972-04-03 | Method for preparing 2,4-dinitro-5-amino-1-x-benzene derivatives |
Country Status (1)
| Country | Link |
|---|---|
| SU (1) | SU436817A1 (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6468999B1 (en) | 1999-07-19 | 2002-10-22 | Pharmacia & Upjohn Company | 1,2,3,4,5,6,-hexahydroazepino [4,5-b]indoles containing arylsulfones at the 9-position |
| US7030109B2 (en) | 1999-07-19 | 2006-04-18 | Pharmacia & Upjohn Company | 1,2,3,4,5,6-Hexahydroazepino[4,5-b]indoles containing arylsulfones at the 9-position |
-
1972
- 1972-04-03 SU SU1767182A patent/SU436817A1/en active
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6468999B1 (en) | 1999-07-19 | 2002-10-22 | Pharmacia & Upjohn Company | 1,2,3,4,5,6,-hexahydroazepino [4,5-b]indoles containing arylsulfones at the 9-position |
| US6878823B2 (en) | 1999-07-19 | 2005-04-12 | Pharmacia & Upjohn Company | 1,2,3,4,5,6-hexahydroazepino[4,5-b]indoles containing arylsulfones at the 9-position |
| US6921823B2 (en) | 1999-07-19 | 2005-07-26 | Pharmacia & Upjohn Company Llc | 1,2,3,4,5,6-Hexahydroazepino[4,5-b]indoles containing arylsulfones at the 9-position |
| US7030109B2 (en) | 1999-07-19 | 2006-04-18 | Pharmacia & Upjohn Company | 1,2,3,4,5,6-Hexahydroazepino[4,5-b]indoles containing arylsulfones at the 9-position |
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