SU278701A1 - METHOD OF OBTAINING ANTHRAHINONIMIDAZOLES - Google Patents
METHOD OF OBTAINING ANTHRAHINONIMIDAZOLESInfo
- Publication number
- SU278701A1 SU278701A1 SU1345800A SU1345800A SU278701A1 SU 278701 A1 SU278701 A1 SU 278701A1 SU 1345800 A SU1345800 A SU 1345800A SU 1345800 A SU1345800 A SU 1345800A SU 278701 A1 SU278701 A1 SU 278701A1
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- anthrahinonimidazoles
- obtaining
- nitrobenzene
- amino
- substituted aromatic
- Prior art date
Links
- LQNUZADURLCDLV-UHFFFAOYSA-N Nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N Chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 150000004982 aromatic amines Chemical class 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000007800 oxidant agent Substances 0.000 description 2
- 238000007243 oxidative cyclization reaction Methods 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- -1 1-piperidino-2-amino-anthraquinone Chemical compound 0.000 description 1
- XOGPDSATLSAZEK-UHFFFAOYSA-N 2-Aminoanthraquinone Chemical compound C1=CC=C2C(=O)C3=CC(N)=CC=C3C(=O)C2=C1 XOGPDSATLSAZEK-UHFFFAOYSA-N 0.000 description 1
- JFTSZLNEIHONSP-UHFFFAOYSA-N C1=CNC=N1.C1=CC=C2C(=O)C3=CC=CC=C3C(=O)C2=C1 Chemical class C1=CNC=N1.C1=CC=C2C(=O)C3=CC=CC=C3C(=O)C2=C1 JFTSZLNEIHONSP-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000003118 aryl group Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000002440 hydroxy compounds Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000001590 oxidative Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002194 synthesizing Effects 0.000 description 1
Description
Изобретение относитс к области получени продуктов, которые могут быть использованы в синтезе красителей.The invention relates to the field of producing products that can be used in the synthesis of dyes.
Известен способ получени арилимидазолов . Способ состоит в том, что о-замещенные ароматические амины, в частности N-алкилированные о-диаминоарилы подвергают окислительной циклизации. В качестве Окислителей используют перекисные кислоты.A known method for the preparation of arylimidazoles. The method consists in the fact that o-substituted aromatic amines, in particular N-alkylated o-diaminoaryls, are subjected to oxidative cyclization. Peroxidic acids are used as oxidizers.
Дл расширени цветовой гаммы красителей предлагаетс способ получени антрахинонимидазолов , заключающийс в том, что о-замещенные ароматические амины-1-диалкиламино- или 1-полиметиленимино-2-аминоантрахиноны подвергают окислительной циклизации. В качестве окислител используют нитробензол.A method for producing anthraquinone imidazoles is proposed to expand the color range of dyes, in that o-substituted aromatic amines-1-dialkylamino or 1-polymethylenimino-2-amino-anthraquinones are subjected to oxidative cyclization. Nitrobenzene is used as an oxidizing agent.
Способ позвол ет получить ранее не описанные продукты.The method allows to obtain products not previously described.
Пример 1. Смесь 0,5 г 1-пиперидино-2аминоантрахинона и 12,5 г нитробензола кип т т в колбе с обратным холодильником 1,5 час. К реакционной смеси, охлажденной до комнатной температуры, приливают при перемешивании 70 мл петролейного эфира (т. кип. 70-100°С). Выпавший осадок отфильтровывают , промывают петролейным эфиро.м от нитробензола, сущат. Выход 0,35 г (70%); т. пл. 248-251°С. После перекристаллизации из хлорбензола получают 8,13-диоксо-1 ,2,3,4,8,13-гексагидропиридо - 1,2-а -антра 2 ,1-й -имидазол в виде желтых игл; т. пл. 250-252°С.Example 1. A mixture of 0.5 g of 1-piperidino-2-amino-anthraquinone and 12.5 g of nitrobenzene is refluxed in a flask for 1.5 hours. To the reaction mixture, cooled to room temperature, is poured with stirring 70 ml of petroleum ether (t. Kip. 70-100 ° C). The precipitation is filtered off, washed with petroleum ether m from nitrobenzene, noun. Yield 0.35 g (70%); m.p. 248-251 ° C. After recrystallization from chlorobenzene, 8,13-dioxo-1, 2,3,4,8,13-hexahydropyrido - 1,2-a-anthra 2, 1 st -imidazole are obtained in the form of yellow needles; m.p. 250-252 ° C.
Найдено, %: С 75,40; 75,22; Н 4,80; 4, 82; N 9,63; 9,50; М 302 (масс-спектроскопически).Found,%: C 75.40; 75.22; H 4.80; 4, 82; N 9.63; 9.50; M 302 (mass spectroscopic).
CigHuN.O,.CigHuN.O ,.
И 4,63; N 9,27;And 4.63; N 9.27;
Вычислено, %: С 75,5; М 302.Calculated,%: C 75.5; M 302.
1-диметиламино-2Пример 2. Смесь 0,4 г аминоантрахинона и 12,5 г щитробензола кип т т 45 час. Охлаждают, раствор несколько раз встр хивают с 5% NaOH (4X20 мл) дл удалени образующихс оксисоединений, нитробензол отгон ют с вод ным паром, осадок отфильтровывают и промывают гор чей водой . Получают 0,3 г (75%) 1-метил-6,М-диоксо-6 ,11 - дигидроантра- 2,1 -1 - имидазола. Желтые иглы; т. пл. 254 - 256°С (из бензола ).1-dimethylamino-2 Example 2. A mixture of 0.4 g of aminoanthraquinone and 12.5 g of schitrobenzene was boiled for 45 hours. The solution is cooled, shaken the solution several times with 5% NaOH (4X20 ml) to remove the resulting hydroxy compounds, the nitrobenzene is distilled off with water vapor, the precipitate is filtered and washed with hot water. Obtain 0.3 g (75%) of 1-methyl-6, M-dioxo-6, 11 - dihydroanthra-2,1 -1 - imidazole. Yellow needles; m.p. 254 - 256 ° С (from benzene).
Найдено, %: С 73,3; 73,5; Н 3,71; 3,81; N 10,9; 11,1.Found,%: C 73.3; 73.5; H 3.71; 3.81; N 10.9; 11.1.
CioHioNaO..CioHioNaO ..
Вычислено, %: С 73,3; Н 3,81; N 10,7.Calculated,%: C 73.3; H 3.81; N 10.7.
Предмет изобретени 3 известным приемом, отличающийс тем, что, с целью расширени цветовой гаммы краентелей , в качестве о-замещенных ароматиче4 ских аминов берут 1-диалкиламино- или 1полиметиленимино-2-аминоантрахиноны , а в качестве окислител берут нитробензол.The subject matter of the invention is 3 in a known manner, characterized in that, in order to expand the color range of the Krales, 1-dialkylamino or 1-polymethyleneimino-2-amino-anthraquinones are taken as o-substituted aromatic amines, and nitrobenzene is taken as oxidant.
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU278701A1 true SU278701A1 (en) |
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