SU184868A1 - METHOD OF OBTAINING 2-NITRO-DERIVATIVES IMIDAZOL - Google Patents
METHOD OF OBTAINING 2-NITRO-DERIVATIVES IMIDAZOLInfo
- Publication number
- SU184868A1 SU184868A1 SU948933A SU948933A SU184868A1 SU 184868 A1 SU184868 A1 SU 184868A1 SU 948933 A SU948933 A SU 948933A SU 948933 A SU948933 A SU 948933A SU 184868 A1 SU184868 A1 SU 184868A1
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- nitro
- derivatives
- imidazol
- obtaining
- imidazole
- Prior art date
Links
- RAXXELZNTBOGNW-UHFFFAOYSA-N Imidazole Chemical compound C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 title description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 8
- WFPZPJSADLPSON-UHFFFAOYSA-N Dinitrogen tetroxide Chemical compound [O-][N+](=O)[N+]([O-])=O WFPZPJSADLPSON-UHFFFAOYSA-N 0.000 description 4
- MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitrogen oxide Substances O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- DRLHVAWTAGOTAU-UHFFFAOYSA-N CC=1N=CNC=1C=NO Chemical compound CC=1N=CNC=1C=NO DRLHVAWTAGOTAU-UHFFFAOYSA-N 0.000 description 2
- VZJVWSHVAAUDKD-UHFFFAOYSA-N Potassium permanganate Chemical compound [K+].[O-][Mn](=O)(=O)=O VZJVWSHVAAUDKD-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- -1 imidazole nitro derivatives Chemical class 0.000 description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 2
- 229910052813 nitrogen oxide Inorganic materials 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- UJGLGHFVENLPLA-UHFFFAOYSA-N 2-(nitromethyl)-1H-imidazole Chemical compound [O-][N+](=O)CC1=NC=CN1 UJGLGHFVENLPLA-UHFFFAOYSA-N 0.000 description 1
- 150000004959 2-nitroimidazoles Chemical class 0.000 description 1
- 230000003115 biocidal Effects 0.000 description 1
- YXHKONLOYHBTNS-UHFFFAOYSA-N diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 230000001717 pathogenic Effects 0.000 description 1
- 244000052769 pathogens Species 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
Description
Изобретение относитс к области получени нитропроизводных имидазола, обладаюи1,их ценными антибиотическими свойствами, например высокой активностью против возбудителей некоторых заболеваний, вызываемых простейшими .The invention relates to the field of production of imidazole nitro derivatives, possessing their valuable antibiotic properties, for example, high activity against pathogens of certain diseases caused by protozoa.
Предлагаемый способ получени 2-нитропроизводных имидазола заключаетс в том, что оксим 4-метил-5-формилимидазола обрабатывают четырехокисью азота при 2-3°С в среде абсолютного ацетонитрила с последую-; щим нагреванием при температуре и выделением продукта известными способами.The proposed method for the preparation of imidazole 2-nitro derivatives consists in that 4-methyl-5-formyl-imidazole oxime is treated with nitrogen tetroxide at 2-3 ° C in absolute acetonitrile medium followed by; heating at a temperature and isolation of the product by known methods.
Пример 1. К суспензии 25 г оксима 4(5)-метил-5(4)-формилимидазола в 950 мл абсолютного ацетонитрила при 2-3°С и перемешивании добавл ют по капл м в течение 4 час раствор 90 мл N-20 (семикратный избыток ) в 250 мл абсолютного ацетонитрила. По окончании прибавлени раствора N904 реакционную смесь перенос т в коническую колбу с обратным воздушным холодильником и нагревают в течение 20-30 мин до 70°С, при этом значительна часть избытка окислов азота выкипает. От реакционной смеси отгон ют растворитель и окислы азота при 20-25°С/ 30 мм, после чего остаток разбавл ют вдвое водой и три раза экстрагируют эфиром по 200 мл. Выпавшие при упаривании эфирных выт жек кристаллы 2-питро-4(5)-метил-5(4)тринитрометилимидазола фильтруют, промывают дважды водой и сушат на воздухе при комнатной температуре.Example 1. To a suspension of 25 g of oxime 4 (5) -methyl-5 (4) -formylimidazole in 950 ml of absolute acetonitrile at 2-3 ° C and a solution of 90 ml of N-20 (4 sevenfold excess) in 250 ml of absolute acetonitrile. Upon completion of the addition of the N904 solution, the reaction mixture is transferred to a conical flask with a reflux air cooler and heated to 70 ° C for 20-30 minutes, with a significant portion of the excess nitrogen oxides boiling over. The solvent and nitrogen oxides were distilled off from the reaction mixture at 20–25 ° C / 30 mm, after which the residue was diluted twice with water and extracted three times with 200 ml of ether. The crystals of 2-pitro-4 (5) -methyl-5 (4) trinitromethylimidazole precipitated upon evaporation of the ether extracts are filtered, washed twice with water and dried in air at room temperature.
Выход 8,47 г, или 15,3о/о от теор., т. пл. 112°С (сразл.).The output of 8.47 g, or 15.3 o / o from theory., So pl. 112 ° C (once).
Пример 2. Действием диазометана в эфире на 2-нитро-4(5)-метил-5(4)-трииитрометилимидазол получают 1,4(5)-диметил-2-нитро-5 (4)-тринитрометилимидазол с выходом 73Vo и т. пл. 110°С (с разл. из метанола).Example 2. By the action of diazomethane in ether on 2-nitro-4 (5) -methyl-5 (4) -trietromethylimidazole, 1,4 (5) -dimethyl-2-nitro-5 (4) -trinitromethylimidazole is obtained with a yield of 73Vo and t pl. 110 ° C (with dec. From methanol).
СаНдЫвОа.SANDWAY.
Пайдено, С 24,82; 25,07; Н 1,94; 2,23; N 28,9; 28,61.Paideno, C 24.82; 25.07; H 1.94; 2.23; N 28.9; 28.61.
Вычислено, о/о: С 24,85; П 2,09; N 28,98. Calculated, o / o: C 24.85; P 2.09; N 28.98.
Пример 3. Действием спиртового раствораExample 3. The action of the alcohol solution
едкого кали и гидроксиламина на 1,4(5)-диметил-2-нитро-5 (4) - тринитрометилимидазолpotassium hydroxide and hydroxylamine on 1,4 (5) -dimethyl-2-nitro-5 (4) - trinitromethylimidazole
на холоду ползчают калиевую соль 1,4(5)-диметил-2-нитро-5 (4)-динитрометилимидазола с1,4 (5) -dimethyl-2-nitro-5 (4) -dinmetromethyl-imidazole potassium salt creeps in the cold
Т. пл. 199°С (с разл. из воды) и выходом .T. pl. 199 ° C (with diff. Out of the water) and the output.
CoHoNsOoK.CoHoNsOoK.
Пайдепо, о/„- С 25,27; 25,52; П 1,99; 2,02; N 24,74; 24,44; К 13,65; 13,8.Paidepo, o / „- C 25.27; 25.52; P 1.99; 2.02; N 24.74; 24.44; K 13.65; 13.8.
Вычислено, С 25,45; Н 2,14; N 24,74; К 13,8.Calculated: C 25.45; H 2.14; N 24.74; K 13.8.
Подкислением водного раствора калиевой 800/0 и т. пл. нитрометилимидазол с выходом 70°С (с разл. из этанола). Пример 4. Кип чением водного раствора калиевой соли 1,4(5,)-диметил-2-нитро-5(4)динитрометилимидазола с перманганатом кали .получают 1,4(5)-диметил - 2 - нитроимидазол-5 (4)-карбоновую кислоту с выходом 490/0 и т. пл. 185-186°С (с разл. из воды). . Найдено, «/о: С 39,05; 39,12; Н 3,75; 3,79; N 22,82; 22,65. Вычислено, С 38,94; Н 3,81; N 22,69. Предмет изобретени Способ получени 2-нитропроизводных имидазола , отличающийс тем, что оксим 4-метил-5-формилимидазола обрабатывают четырехокисью азота при 2-3°С в среде абсолютного ацетонитрила с последующим нагреванием при температуре 70°С и выделением продукту известными способами.Acidification of an aqueous solution of potassium 800/0 and so on. Pl. nitromethyl imidazole with a yield of 70 ° C (with dec. from ethanol). Example 4. By boiling an aqueous solution of 1,4 (5,) - dimethyl-2-nitro-5 (4) dinitromethylimidazole potassium salt with potassium permanganate, 1,4 (5) -dimethyl -2 - nitroimidazole-5 (4) is obtained -carboxylic acid with a yield of 490/0, and so on. PL. 185-186 ° С (with debris from water). . Found, "/ o: C 39.05; 39.12; H 3.75; 3.79; N 22.82; 22.65. Calculated C, 38.94; H 3.81; N 22.69. The subject of the invention is a process for the preparation of 2-nitro-imidazole derivatives, characterized in that 4-methyl-5-formyl imidazole oxime is treated with nitrogen tetroxide at 2-3 ° C in absolute acetonitrile, followed by heating at 70 ° C and isolating the product by known methods.
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU184868A1 true SU184868A1 (en) |
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