SU252346A1 - METHOD OF OBTAINING 2,4,6-TRYNITROBENZOYLHYDRASIDE - Google Patents
METHOD OF OBTAINING 2,4,6-TRYNITROBENZOYLHYDRASIDEInfo
- Publication number
- SU252346A1 SU252346A1 SU1256733A SU1256733A SU252346A1 SU 252346 A1 SU252346 A1 SU 252346A1 SU 1256733 A SU1256733 A SU 1256733A SU 1256733 A SU1256733 A SU 1256733A SU 252346 A1 SU252346 A1 SU 252346A1
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- trinitrobenzoyl
- trynitrobenzoylhydraside
- obtaining
- synthesis
- hydrazide
- Prior art date
Links
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine hydrate Chemical compound O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 7
- -1 aromatic ones Chemical class 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- 230000002194 synthesizing Effects 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- MWGGWCCALVNFPN-UHFFFAOYSA-N 2,4,6-trinitrobenzoyl chloride Chemical compound [O-][N+](=O)C1=CC([N+]([O-])=O)=C(C(Cl)=O)C([N+]([O-])=O)=C1 MWGGWCCALVNFPN-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N acetic acid ethyl ester Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000000575 pesticide Substances 0.000 description 3
- VZGDMQKNWNREIO-UHFFFAOYSA-N Carbon tetrachloride Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N Chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 229940042795 Hydrazides for tuberculosis treatment Drugs 0.000 description 2
- QRXWMOHMRWLFEY-UHFFFAOYSA-N Isoniazid Chemical group NNC(=O)C1=CC=NC=C1 QRXWMOHMRWLFEY-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- KAQBNBSMMVTKRN-UHFFFAOYSA-N 2,4,6-trinitrobenzoic acid Chemical compound OC(=O)C1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O KAQBNBSMMVTKRN-UHFFFAOYSA-N 0.000 description 1
- WHHNFHDJLGLCHO-UHFFFAOYSA-N 2,5-bis(2,4,6-trinitrophenyl)-1,3,4-oxadiazole Chemical compound [O-][N+](=O)C1=CC([N+](=O)[O-])=CC([N+]([O-])=O)=C1C1=NN=C(C=2C(=CC(=CC=2[N+]([O-])=O)[N+]([O-])=O)[N+]([O-])=O)O1 WHHNFHDJLGLCHO-UHFFFAOYSA-N 0.000 description 1
- ORLIFVYIUIQGOA-UHFFFAOYSA-N N'-(4-nitrosophenyl)benzohydrazide Chemical compound C1=CC(N=O)=CC=C1NNC(=O)C1=CC=CC=C1 ORLIFVYIUIQGOA-UHFFFAOYSA-N 0.000 description 1
- 210000004940 Nucleus Anatomy 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- XDLDASNSMGOEMX-UHFFFAOYSA-N benzene benzene Chemical compound C1=CC=CC=C1.C1=CC=CC=C1 XDLDASNSMGOEMX-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N fumaric acid Chemical compound OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 201000008827 tuberculosis Diseases 0.000 description 1
Description
Гидразиды наход т широкое применение как биологически активные (противотуберкулезные и другие) вещества; как пестициды разнообразного назначени (церенокс, тидразид малеиновой кислоты, иирамин и т. д.), как исходные соединени при синтезе «биологически активных вендеств, пестицидов, термостойких и термопластичных полимеров и других соединений . Несмотр .на это, хими гидразидов полинитрокарбоновых кислот, в том числе и ароматических , изучена чрезвычайно мало. Наличие в молекуле нитрогрупл и гидразидиой группировки дать новые неожиданные свойства и послужить .исходными соединени ми .дл получени целого р да перспективных веществ, не выдел емых при синтезе другими пут ми. Одним из таких интересных и перспективных веществ вл етс 2,4,6-тринитробензоилгидразид , который может найти применение как самосто тельное вещество и который использован дл синтеза 2,5-дипикрил-1,3,4-оксадиазола , а также может примен тьс дл синтеза красителей, пестицидов и биологически активных веществ. 2,4,6-Тринитробензоилгидразид синтезирован взаимодействием 2,4,6-тринитробензоилхлорида с водным гидразингидратом в среде бензола при небольшом нагревании. Исходна 2,4,6-тринитробензойна кислота, используема дл получени хлорангидрида ее, получаетс окислением тротила и, Cv1eдoйaтельно , имеет обеспеченную сырьевую базу, а также разработанные дл промышленных условий методы производства. Гидразингидрат вл етс продуктом многотоннажного производства . Пример. Синтез 2,4,6-т р и н и т р о б е н3 о и л г и д р а 3 и д а. К раствору 1,4 г (0,005 г-моль) 2,4,6-тринитробензоилхлорида в 35 мл бензола ири перемешивании прикапывают раствор 0,6 г (0,011 г моль) 859/о-ного гидразингидрата в 5 мл воды при 15-20 С. Через 30 мин температуру поднимают до 40- 45° С и выдерживают 10 мин. После охлаждени до комнатной температуры добавл ют 25 мл воды и осадок отфильтровывают, промывают водой 1 сушат. Получают 1,1 г (80% от теоретического) желтых иголок с т. пл. 187-188° С (из воды), хорошо растворимых в спиртах, ацетоне, диоксане, гор чей воде, плохо - в четыреххлористом углероде, бензоле и хлорбензоле. Найдено, %: С 30,31; 30,20; Н 2,00; 2,01; N 25,42; 25,30. . Вычислено, %: С 30,99; Н 1,84; N 25,83. ПК-спектр (), .CM-I: 3280 (NH), 1668 (СО), 1609 ( дро), 1517 и 1353 (NOg). 2,4,6-Тринитробензоилгидразои ацетона получают кип чением гидразида и ацетона в БОде . Мелкие листочки с т. нл. 221-222° С (из спирта) хорошо растворимы в ацетоне, диоксаие , этилац етате, плохо вводе и бензоле. Найдено, %: С 38,85; 38,37; Н 3,00; 2,91; N 22,04; 21,86. . . Вычислено, %: С 38,46; Н 2,88; N 22,50. ИК-спектр (HR-IO), 3219 (Nli), 2860 (СНз), 1673 (СО), 1609 ( дро), 1547 и 1350 (NOs), 1296 и 1268 (С-N). Предмет i з о б р е т е н и Способ получени 2,4,6-тринитробензоилгидразида , отличающийс тем, что 2,4,6-тринитробензоилхлорид подвергают взаимодействию с гидразингидратом в среде инертного органического растворител с последующим выделением целевого продукта известными ириемами . Считать приоритет от 9.X. 1967 согласие за вке К° 1189287/23-4.Hydrazides are widely used as biologically active (tuberculosis and other) substances; as various purpose pesticides (tserenox, maleic acid thidrazide, iyramine, etc.), as starting compounds in the synthesis of biologically active substances, pesticides, heat-resistant and thermoplastic polymers and other compounds. Despite this, the chemistry of hydrazides of polynitrocarboxylic acids, including aromatic ones, is extremely little studied. The presence of nitro-groups and hydrazide groups in the molecule will give new unexpected properties and serve as the original compounds to produce a number of promising substances that are not isolated during the synthesis by other means. One of such interesting and promising substances is 2,4,6-trinitrobenzoyl hydrazide, which can be used as an independent substance and which is used for the synthesis of 2,5-dipicryl-1,3,4-oxadiazole, and can also be used for synthesis of dyes, pesticides and biologically active substances. 2,4,6-Trinitrobenzoyl hydrazide was synthesized by reacting 2,4,6-trinitrobenzoyl chloride with aqueous hydrazine hydrate in benzene with slight heating. The original 2,4,6-trinitrobenzoic acid, used to obtain its acid chloride, is obtained by oxidation of TNT and, Cv1 is more efficient, has a provided raw material base, as well as production methods developed for industrial conditions. Hydrazine hydrate is a product of heavy production. Example. Synthesis of 2,4,6-t r and n and t r about b e N 3 o and l g and d r a 3 and d a. To a solution of 1.4 g (0.005 g-mol) of 2,4,6-trinitrobenzoyl chloride in 35 ml of benzene and stirring, a solution of 0.6 g (0.011 g mol) of 859 / o-hydrazine hydrate in 5 ml of water at 15-20 is added dropwise. C. After 30 minutes the temperature is raised to 40-45 ° C and held for 10 minutes. After cooling to room temperature, 25 ml of water are added and the precipitate is filtered off, washed with water 1 and dried. Obtain 1.1 g (80% of theoretical) yellow needles with m. Pl. 187-188 ° С (from water), soluble in alcohols, acetone, dioxane, hot water, poorly - in carbon tetrachloride, benzene and chlorobenzene. Found,%: C 30.31; 30.20; H 2.00; 2.01; N 25.42; 25.30. . Calculated,%: C 30.99; H 1.84; N 25.83. PC spectrum (), .CM-I: 3280 (NH), 1668 (CO), 1609 (nuclei), 1517 and 1353 (NOg). 2,4,6-Trinitrobenzoylhydrase of acetone is obtained by boiling hydrazide and acetone in God. Small leaves with t. Nl. 221-222 ° С (from alcohol) are well soluble in acetone, dioxia, ethyl acetate, poorly added, and benzene. Found,%: C 38.85; 38.37; H 3.00; 2.91; N 22.04; 21.86. . . Calculated,%: C 38.46; H 2.88; N 22.50. IR (HR-IO), 3219 (Nli), 2860 (CH3), 1673 (CO), 1609 (draw), 1547 and 1350 (NOs), 1296 and 1268 (C-N). Subject of claim and Method for producing 2,4,6-trinitrobenzoyl hydrazide, characterized in that 2,4,6-trinitrobenzoyl chloride is reacted with hydrazine hydrate in an inert organic solvent medium, followed by isolation of the target product with known iriemems. Read priority from 9.X. 1967 agreement of the application K ° 1189287 / 23-4.
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU252346A1 true SU252346A1 (en) |
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