RU2009149019A - METHOD FOR PRODUCING SUBSTITUTED 4- [CYANO (PHENYL) METHYL] -5-NITROPHTHALONITRILES BASED ON 4-BROM-5-NITROPHTHALONITRIL - Google Patents
METHOD FOR PRODUCING SUBSTITUTED 4- [CYANO (PHENYL) METHYL] -5-NITROPHTHALONITRILES BASED ON 4-BROM-5-NITROPHTHALONITRIL Download PDFInfo
- Publication number
- RU2009149019A RU2009149019A RU2009149019/04A RU2009149019A RU2009149019A RU 2009149019 A RU2009149019 A RU 2009149019A RU 2009149019/04 A RU2009149019/04 A RU 2009149019/04A RU 2009149019 A RU2009149019 A RU 2009149019A RU 2009149019 A RU2009149019 A RU 2009149019A
- Authority
- RU
- Russia
- Prior art keywords
- nitrophthalonitriles
- cyano
- phenyl
- methyl
- substituted
- Prior art date
Links
- PZOBMISAMQBXIY-UHFFFAOYSA-N 4-bromo-5-nitrobenzene-1,2-dicarbonitrile Chemical compound [O-][N+](=O)C1=CC(C#N)=C(C#N)C=C1Br PZOBMISAMQBXIY-UHFFFAOYSA-N 0.000 title 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 title 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical class [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 title 1
- 238000004519 manufacturing process Methods 0.000 title 1
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical class [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 title 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims abstract 6
- 239000002244 precipitate Substances 0.000 claims abstract 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims abstract 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract 2
- 239000003480 eluent Substances 0.000 claims abstract 2
- 230000003993 interaction Effects 0.000 claims abstract 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract 2
- 239000000741 silica gel Substances 0.000 claims abstract 2
- 229910002027 silica gel Inorganic materials 0.000 claims abstract 2
- 159000000000 sodium salts Chemical class 0.000 claims abstract 2
- 239000002904 solvent Substances 0.000 claims abstract 2
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Способ получения замещенных 4-[циано(фенил)метил]-5-нитрофталонитрилов общей формулы: ! ! заключающийся в том, что 4-бром-5-нитрофталонирил подвергают взаимодействию с натриевыми солями 2-замещенных оксобутенитрилов при мольном соотношении 1:2 соответственно, при температуре T=19…25°C в течение 1-2 ч в растворе ДМФА, после чего реакционную массу разбавляют десятикратным избытком воды с T=0…25°C, выделившийся смолистый осадок экстрагируют хлористым метиленом, тщательно промывают водой, хроматографируют на силикогеле, элюент (растворитель) упаривают, а выпавший осадок отфильтровывают и перекристаллизовывают из спирта. The method of obtaining substituted 4- [cyano (phenyl) methyl] -5-nitrophthalonitriles of the General formula:! ! consisting in the fact that 4-bromo-5-nitrophthaloniril is subjected to interaction with the sodium salts of 2-substituted oxobutenitriles in a molar ratio of 1: 2, respectively, at a temperature of T = 19 ... 25 ° C for 1-2 hours in a DMF solution, after which the reaction mass is diluted with a tenfold excess of water with T = 0 ... 25 ° C, the gummy precipitate formed is extracted with methylene chloride, washed thoroughly with water, chromatographed on silica gel, the eluent (solvent) is evaporated, and the precipitate formed is filtered off and recrystallized from alcohol.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| RU2009149019/04A RU2428413C1 (en) | 2009-12-28 | 2009-12-28 | Method of producing substituted 4-[cyano(phenyl)methyl]-5-nitrophthalonitriles based on 4-bromo-5-nitrophthalonitrile |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| RU2009149019/04A RU2428413C1 (en) | 2009-12-28 | 2009-12-28 | Method of producing substituted 4-[cyano(phenyl)methyl]-5-nitrophthalonitriles based on 4-bromo-5-nitrophthalonitrile |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU2009149019A true RU2009149019A (en) | 2011-07-10 |
| RU2428413C1 RU2428413C1 (en) | 2011-09-10 |
Family
ID=44739919
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2009149019/04A RU2428413C1 (en) | 2009-12-28 | 2009-12-28 | Method of producing substituted 4-[cyano(phenyl)methyl]-5-nitrophthalonitriles based on 4-bromo-5-nitrophthalonitrile |
Country Status (1)
| Country | Link |
|---|---|
| RU (1) | RU2428413C1 (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2534990C1 (en) * | 2013-07-19 | 2014-12-10 | Федеральное государственное бюджетное образовательное учреждение высшего профессионального образования "Ярославский государственный технический университет" (ФГБОУВПО "ЯГТУ") | Method of producing 4-[2-chloro-1-formyl-2-r-vinyl]-5-nitrophthalonitriles |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2260016C1 (en) * | 2004-01-06 | 2005-09-10 | Институт синтетических полимерных материалов (ИСПМ) им. Н.С. Ениколопова РАН | Super-branched polyimides and 4,5-bis-(3-aminophenoxy)phthalic acid for their preparing |
| RU2266286C1 (en) * | 2004-07-20 | 2005-12-20 | Ярославский государственный технический университет | Heterocyclic ortho-dicarbonitriles |
-
2009
- 2009-12-28 RU RU2009149019/04A patent/RU2428413C1/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| RU2428413C1 (en) | 2011-09-10 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EA201070186A1 (en) | METHODS AND CONNECTIONS INTENDED TO OBTAIN STERN-GLUCOSE TYPE 2 INHIBITORS | |
| RU2017102355A (en) | METHOD FOR PRODUCING A CONDENSED HETEROCYCLIC COMPOUND | |
| RU2010145171A (en) | ANALOGUES OF GALIHONDRIN IN | |
| EA201000642A1 (en) | 2'-FLUOR-2'-DEOXYTETRAHYDROUridine AS CYTIDINDE DIAMINASE INHIBITORS | |
| PE20120617A1 (en) | PROCESSES TO PREPARE COBICISTAT AND ITS INTERMEDIATE PRODUCTS | |
| RU2011133749A (en) | METHOD FOR PRODUCING AND ISOLATING 2-ACYLAMIN-3-DIPHENYL PROPIONIC ACID | |
| EA201070437A2 (en) | METHOD OF OBTAINING 2'-DEOXY-5-AZACYTIDINE (Decitabine) | |
| RU2009149019A (en) | METHOD FOR PRODUCING SUBSTITUTED 4- [CYANO (PHENYL) METHYL] -5-NITROPHTHALONITRILES BASED ON 4-BROM-5-NITROPHTHALONITRIL | |
| RU2015128095A (en) | METHOD FOR PRODUCING 4-AMINO-5-FLUOR-3-CHLORINE-6- (SUBSTITUTED) PICOLINATES | |
| RU2011143166A (en) | NEW CRYSTAL FORMS OF ADEFOVIR DIPIVOXIL AND METHODS OF ITS PRODUCTION | |
| AR075441A1 (en) | A PROCESS FOR THE PREPARATION OF ETORICOXIB | |
| RU2015130337A (en) | METHOD FOR PRODUCING FLUORACTON DERIVATIVE | |
| RU2010120061A (en) | METHOD FOR PRODUCING SUBSTITUTED 4-NITRO-5- (2-OXOETHYL) PHTHALONITRILES | |
| RU2013129036A (en) | A NEW METHOD FOR OBTAINING ANTIFOLATE AGENTS WITH A GLUTAMINIC ACID FRAGMENT IN ITS STRUCTURE | |
| RU2009102442A (en) | METHOD FOR PRODUCING SUBSTITUTED BENZOFURAN-5,6-DICARBONITRILES | |
| RU2010120060A (en) | METHOD FOR PRODUCING 3-SUBSTITUTED 1,2-BENZISOXOXAZOL-5,6-DICARBONITRILES | |
| RU2015117526A (en) | METHOD FOR PRODUCING ALCOXICARBONYLISOTHYOTIOCIANATE | |
| RU2013136474A (en) | 2-MERCAPTOBENZTELLURAZOLE AND METHOD FOR PRODUCING THEM | |
| AR082159A1 (en) | PROCESS FOR THE PREPARATION OF ENOLATE SALTS OF 4-FLUORO-2-HYDROXIMETHYLENE-3-OXO-BUTIRATES | |
| RU2010120062A (en) | METHOD FOR PRODUCING ETHERS OF SUBSTITUTED 5,6-DICYANOBENZOFURAN-2-CARBOXYLIC ACIDS | |
| RU2007139616A (en) | METHOD FOR PRODUCING CIS-DICHLORODIMETHYLAMIN PLATINUM (II) | |
| MX2022001145A (en) | CONTINUOUS PROCESS TO PREPARE THE CRYSTALLINE FORM II OF SOTAGLIFLOZIN. | |
| BR112017005454A2 (en) | sodium glucose transporter inhibitor 2 l-proline compound, and l-proline compound monohydrate and crystal | |
| RU2013135609A (en) | INTEGRATED COMPOUND OF ORGANIC ACID DERIVATED METHYLURACYL AND METHOD FOR ITS PRODUCTION | |
| RU2436765C1 (en) | Method of producing 2,3-dimethyl-2,3-dinitrobutane |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM4A | The patent is invalid due to non-payment of fees |
Effective date: 20131229 |