SU16200A1 - Method for producing quinoid derivatives of 2: 1 naphtho-phenothiazine - Google Patents
Method for producing quinoid derivatives of 2: 1 naphtho-phenothiazineInfo
- Publication number
- SU16200A1 SU16200A1 SU17641A SU17641A SU16200A1 SU 16200 A1 SU16200 A1 SU 16200A1 SU 17641 A SU17641 A SU 17641A SU 17641 A SU17641 A SU 17641A SU 16200 A1 SU16200 A1 SU 16200A1
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- naphtho
- phenothiazine
- producing
- derivatives
- quinoid derivatives
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title description 2
- CGXNXSVUIRWLOF-UHFFFAOYSA-N 10-thia-3-azapentacyclo[12.8.0.02,11.04,9.015,20]docosa-1(14),2(11),4,6,8,12,15,17,19,21-decaene Chemical compound C1=CC=C2C3=CC=C4SC5=CC=CC=C5NC4=C3C=CC2=C1 CGXNXSVUIRWLOF-UHFFFAOYSA-N 0.000 title 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 238000000034 method Methods 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 2
- -1 (o-nitrophenylmercapto) -1, 4-naphthoquinone Chemical compound 0.000 description 1
- FRASJONUBLZVQX-UHFFFAOYSA-N 1,4-naphthoquinone Chemical compound C1=CC=C2C(=O)C=CC(=O)C2=C1 FRASJONUBLZVQX-UHFFFAOYSA-N 0.000 description 1
- JIZRGGUCOQKGQD-UHFFFAOYSA-N 2-nitrothiophene Chemical compound [O-][N+](=O)C1=CC=CS1 JIZRGGUCOQKGQD-UHFFFAOYSA-N 0.000 description 1
- AGIJRRREJXSQJR-UHFFFAOYSA-N 2h-thiazine Chemical group N1SC=CC=C1 AGIJRRREJXSQJR-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- 241000723347 Cinnamomum Species 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 238000004061 bleaching Methods 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000003518 caustics Substances 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 235000017803 cinnamon Nutrition 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 159000000011 group IA salts Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 238000007747 plating Methods 0.000 description 1
- 235000021395 porridge Nutrition 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000011946 reduction process Methods 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 150000004897 thiazines Chemical class 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Предлагаемый способ получени хиноидных производных 2, 1-нафтофенотиазина oCHOBiaH на восстановленни 2-Ьксн3 ,2-ннтрофе1нилмер капто-1, 4-нафтахинона или его амидбпроизводных иАи сульфО йслот и последующем выделении производных 2, 1-нафтофенотиазина из смеси обычным приёмом.The proposed method for the preparation of quinoid derivatives of 2, 1-naphtofenothiazine oCHOBiaH on a reduced 2-ntfcfxn3, 2-ntrofeylnylmer capto-1, 4-naphtaquinone or its amide derivatives and A and sulfoneic acids and the subsequent isolation of the derivatives of 2, 1 nfto cf and A and sulphonoslot, and the subsequent separation of the 2, 1 -flutoph derivatives and Ai and sulphonoslot and the subsequent separation of the 2, 1-naphtophin derivatives and A and sulfone eslot and the subsequent separation of the 2, 1 derivatives, and 5-naphtaquinone;
При этом происходит замыкание тиазинового кольца: .When this occurs, the closure of the thiazine ring:.
ОНHE
Смотр цо веществу, вз тому дл восстановлени , замыкание кольца происходит уже при процессе восстановлени или при последующем пбдкислении.,Looking at the material as it is taken up for reduction, the ring closure occurs already during the reduction process or during the subsequent acidification,
2-окси- 3, 21-нитрофенилмеркапто-1, 4нафтохинон можно получить, разлага 2-ариламиноили 2-ацедиламино-3 хлор-1, 4-нафтахинон 2-нитротиофен6лом и замеща аминогруппу гидроксилом при кип чении со щелочами. Соединение это представл ет собою рко блест щий оранжево-красный кристаллический порошок с температурой плавлени в 245 , раствор ющийс в концентрированной серной кислоте и щелочах с оранжево-желтым.. цветом. С избыточным гидратом окиси натра лолучаетс натриева Г соль блест ще медного цвета. Путем обработки слабо дым щейс серной кислотой на холоду получают легко растворимую в воде сульфокислоту оранжево-желтого цвета.2-hydroxy-3, 21-nitrophenyl mercapto-1, 4 naphthoquinone can be obtained by decomposing 2-arylamino or 2-acedylamino-3 chloro-1, 4-naphtaquinone 2-nitrothiophene, and replacing the amino group with hydroxyl by boiling with alkalis. This compound is a brightly bright orange-red crystalline powder with a melting point of 245, dissolved in concentrated sulfuric acid and alkalis with an orange-yellow color. With excess sodium hydrate, sodium salt is obtained brilliantly copper-colored. By treating lightly smoked sulfuric acid in the cold, water-soluble orange-yellow sulphonic acid is obtained.
Пример, 33 части 2-окси-З- (о-ннтрофенилмеркапто )-, 4-нафтохинона раствор ютс на холоду с 13 чacт fйи натронной щелочи 40° В6 в 100 част х вод к раствору /добавл ют около 7 частей гидросульфита натра до обесцвечивани . Пропускают воздух до тех пор, покаExample 33 parts of 2-hydroxy-3- (o-ntrophenylmercapto) -, 4-naphthoquinone are dissolved in the cold from 13 hours of sodium and sodium alkaline 40 ° B6 in 100 parts of water to the solution / about 7 parts of sodium hydrosulfite are added until bleaching . Let air through until
раствор не станет темно-корнчевым, и подкисл ют . .Жидкость спущаетс , особенно легко при нагревании, в кашеобразную массу фиолетового цвета, состо щую из деривата тиазина. Последний представл ет собой кристаллический фиолетовый порошок, Дающий в концентрированной серной кислоте раствор коричневофирлетэвой окраски. В разведенных paiCTBOpax едких щелочей он дает нестойкий раствор зелено-синего цвета,-изthe solution will not turn dark cinnamon, and acidify. The liquid descends, especially when heated, into a purple-colored porridge mass consisting of a thiazine derivative. The latter is a crystalline violet powder, giving a solution of brown furlet color in concentrated sulfuric acid. In diluted paiCTBOpax caustic alkalis, it gives an unstable solution of green-blue color, - of
которого выдел етс трудно раствЬрима; щелочна соль темно-синего цвета.which is difficult to dissolve; alkaline salt of dark blue.
Если исходить из сульфокислоты 2 5кси-3 . (о-нитрофенилмеркапто)-1, 4-нафтохинона , то получают, примен тот же прием, тиазинсульфокислоту, окрашивающудо шерсть в фиолеторо-ткрасный цвет, при последующем хромировании переход щий в более зеЛеный оттенок. Подобные же: результаты дают продукты замещени вышеуказанного исходного материала .Предмет патента.If we start from sulfonic acid 2 5xy-3. (o-nitrophenylmercapto) -1, 4-naphthoquinone, you get, using the same technique, thiazinsulfonic acid, dyeing the wool in a violet-red color, with subsequent chromium plating into a greener shade. Similar: results give the products of the replacement of the above starting material. Subject of the patent.
Способ получени хйноидных производнь1х 2, 1-нафтофенотиазина, отличайщийс тем, что 2-окси-З, 2-нитрофенилмеркапто-1 ,4-нафтохинон или его амидопроизвЪдные , или рульфокислоты подвергают действию восстановителей, после чего полученные производные 2, 1-нафтофенотиазина вьгдел ют из реакционной смеси, обычными приемами.A process for preparing hynoidnyh proizvodn1h 2, 1-naftofenotiazina, otlichayschiys in that the 2-hydroxy-W, 2-nitrofenilmerkapto-1, 4-naphthoquinone or its amidoproizvdnye or rulfokisloty subjected to the action of reducing agents, after which the obtained derivative 2, 1-naftofenotiazina vgdel dissolved from the reaction mixture, the usual methods.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SU17641A SU16200A1 (en) | 1926-09-13 | 1926-09-13 | Method for producing quinoid derivatives of 2: 1 naphtho-phenothiazine |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SU17641A SU16200A1 (en) | 1926-09-13 | 1926-09-13 | Method for producing quinoid derivatives of 2: 1 naphtho-phenothiazine |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU16200A1 true SU16200A1 (en) | 1930-08-31 |
Family
ID=48336685
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU17641A SU16200A1 (en) | 1926-09-13 | 1926-09-13 | Method for producing quinoid derivatives of 2: 1 naphtho-phenothiazine |
Country Status (1)
| Country | Link |
|---|---|
| SU (1) | SU16200A1 (en) |
-
1926
- 1926-09-13 SU SU17641A patent/SU16200A1/en active
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