SU486018A1 - The method of obtaining 1-aryl-2- / p-aminophenyl / -5-aminobenzimidazoles - Google Patents
The method of obtaining 1-aryl-2- / p-aminophenyl / -5-aminobenzimidazolesInfo
- Publication number
- SU486018A1 SU486018A1 SU1980999A SU1980999A SU486018A1 SU 486018 A1 SU486018 A1 SU 486018A1 SU 1980999 A SU1980999 A SU 1980999A SU 1980999 A SU1980999 A SU 1980999A SU 486018 A1 SU486018 A1 SU 486018A1
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- aminophenyl
- aminobenzimidazoles
- aryl
- obtaining
- alcohol
- Prior art date
Links
Description
хлорида. Смесь продуктов сплавл ют при 165-170°С в течение 1,5 час. Полученную твердую массу обрабатывают 10%-ным раствором соды дл удалени остатков п-нитробензоилхлорида . Получают 7,5 г (91%) вещества; т. пл. 218-220°С (из смеси изомеров ксилола). Найдено, %: С 60,39, 60,68; И 3,59, 3,43; N 14,80. Ci9ni4N405. Вычислено, %: С 60,31; Н 3,73; N 14.81. Rf 0,8 (элюент - спирт : бензол, 1:8). Вещество раствор етс в спиртах, диоксане, диметилформамиде; не раствор етс в эфире, бензоле. Ямакс 262 нм (Ige 4,49), Ямакс 385 нм (Igs 4,38) (в спирте). 1-феиил-2-(п-аминофенил) - 5 - аминобеизимидазол . К раствору 9,42 г SnCl2-2H2O в 50 мл концентрированной сол ной кислоты, нагретому до 70°С, в течение 15 мин добавл ют 2 г 4-нитро-2 - (л-нитробензоил) - аминодифениламина . Реакционную массу кин т т в течение 2 час. К концу кип чени все переходит в раствор. Его охлаждают, выпавший осадок отфильтровывают , раствор ют в воде и подщелачивают 10%-ным раствором едкого натра до рН 9,5-10. Получают 1,33 г (84%) вещества; т. пл. 267-268°С (из 50%-ного спирта). Найдено, %: С 75,26, 75,68; Н 5,89, 5,63; N 18,31, 18,29. Ci9HieN4. Вычислено, %: С 76,0; Н 5,33; N 18,67. Rf 0,84 (спирт : бензол 1:5). ччакс 285 нм (Ige 4,18); Хмакс 335 им (Ige 4,23). Растворитель - спирт. Вещество раствор етс в спиртах, диоксане, диметилформамиде, не раствор етс в эфире, гептане. 4 Предмет изобретений 1. Способ получени 1-арил-2-(п-аминофенил )-5-аминобензимидазолов общей формулы I т, (О где Аг - фенил, а-нафтил или р-антрахинонил , отличающийс тем, что о-фенилендиамин общей формулы П де Аг имеет указанные значени , подвергат взаимодействию с хлорангидридом п-нитобензойной кислоты и полученный анилид общей формулы П1 осстанавливают двухлористым оловом в со ной кислоте. 2. Способ по п. 1, отличающийс тем, то конденсацию хлорангидрида нитробензойой кислоты с соединением формулы П осуествл ют при 165-170°С.chloride. The mixture of products is fused at 165-170 ° C for 1.5 hours. The resulting solid mass is treated with a 10% soda solution to remove residues of p-nitrobenzoyl chloride. 7.5 g (91%) of the substance are obtained; m.p. 218-220 ° C (from a mixture of xylene isomers). Found,%: C 60.39, 60.68; And 3.59, 3.43; N 14.80. Ci9ni4N405. Calculated,%: C 60.31; H 3.73; N 14.81. Rf 0.8 (eluent alcohol: benzene, 1: 8). The substance is soluble in alcohols, dioxane, dimethylformamide; not soluble in ether, benzene. Yamax 262 nm (Ige 4.49), Yamax 385 nm (Igs 4.38) (in alcohol). 1-feiyl-2- (p-aminophenyl) - 5 - aminobeisimidazole. To a solution of 9.42 g of SnCl2-2H2O in 50 ml of concentrated hydrochloric acid heated to 70 ° C, 2 g of 4-nitro-2 - (l-nitrobenzoyl) - aminodiphenylamine are added over 15 minutes. The reaction mass kin t t for 2 hours. By the end of the boil everything goes into solution. It is cooled, the precipitated precipitate is filtered off, dissolved in water and alkalinized with 10% sodium hydroxide solution to a pH of 9.5-10. 1.33 g (84%) of the substance are obtained; m.p. 267-268 ° C (from 50% alcohol). Found,%: C 75.26, 75.68; H 5.89, 5.63; N 18.31, 18.29. Ci9HieN4. Calculated,%: C 76.0; H 5.33; N 18.67. Rf 0.84 (alcohol: benzene 1: 5). Chchaks 285 nm (Ige 4.18); Hmax 335 im (Ige 4.23). Solvent - alcohol. The substance is soluble in alcohols, dioxane, dimethylformamide, does not dissolve in ether, heptane. 4 Subject of the inventions 1. A method for producing 1-aryl-2- (p-aminophenyl) -5-aminobenzimidazoles of the general formula I t P de Ar has the indicated values, is reacted with p-nitobenzoic acid chloride and the resulting anilide of the general formula P1 is reduced with tin dichloride in hydrochloric acid. 2. The method of claim 1, wherein at 165-170 ° C.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SU1980999A SU486018A1 (en) | 1973-12-29 | 1973-12-29 | The method of obtaining 1-aryl-2- / p-aminophenyl / -5-aminobenzimidazoles |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SU1980999A SU486018A1 (en) | 1973-12-29 | 1973-12-29 | The method of obtaining 1-aryl-2- / p-aminophenyl / -5-aminobenzimidazoles |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU486018A1 true SU486018A1 (en) | 1975-09-30 |
Family
ID=20571003
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU1980999A SU486018A1 (en) | 1973-12-29 | 1973-12-29 | The method of obtaining 1-aryl-2- / p-aminophenyl / -5-aminobenzimidazoles |
Country Status (1)
| Country | Link |
|---|---|
| SU (1) | SU486018A1 (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1998024776A1 (en) * | 1996-12-06 | 1998-06-11 | The Dow Chemical Company | Preparation of an aminoarylaminoarazole |
| CN109400536A (en) * | 2018-12-21 | 2019-03-01 | 东华大学 | A kind of N substituted benzimidazole diamines and preparation method thereof |
-
1973
- 1973-12-29 SU SU1980999A patent/SU486018A1/en active
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1998024776A1 (en) * | 1996-12-06 | 1998-06-11 | The Dow Chemical Company | Preparation of an aminoarylaminoarazole |
| CN109400536A (en) * | 2018-12-21 | 2019-03-01 | 东华大学 | A kind of N substituted benzimidazole diamines and preparation method thereof |
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