RU2010120062A - METHOD FOR PRODUCING ETHERS OF SUBSTITUTED 5,6-DICYANOBENZOFURAN-2-CARBOXYLIC ACIDS - Google Patents
METHOD FOR PRODUCING ETHERS OF SUBSTITUTED 5,6-DICYANOBENZOFURAN-2-CARBOXYLIC ACIDS Download PDFInfo
- Publication number
- RU2010120062A RU2010120062A RU2010120062/04A RU2010120062A RU2010120062A RU 2010120062 A RU2010120062 A RU 2010120062A RU 2010120062/04 A RU2010120062/04 A RU 2010120062/04A RU 2010120062 A RU2010120062 A RU 2010120062A RU 2010120062 A RU2010120062 A RU 2010120062A
- Authority
- RU
- Russia
- Prior art keywords
- dicyanobenzofuran
- substituted
- carboxylic acids
- water
- precipitate
- Prior art date
Links
- HRXGGJBVQYIQLS-UHFFFAOYSA-N 5,6-dicyano-1-benzofuran-2-carboxylic acid Chemical class C(#N)C=1C(=CC2=C(C=C(O2)C(=O)O)C=1)C#N HRXGGJBVQYIQLS-UHFFFAOYSA-N 0.000 title claims abstract 5
- 150000002170 ethers Chemical class 0.000 title 1
- 238000004519 manufacturing process Methods 0.000 title 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims abstract 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims abstract 6
- 239000003153 chemical reaction reagent Substances 0.000 claims abstract 4
- 150000002148 esters Chemical class 0.000 claims abstract 4
- 239000002244 precipitate Substances 0.000 claims abstract 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract 4
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims abstract 2
- PZOBMISAMQBXIY-UHFFFAOYSA-N 4-bromo-5-nitrobenzene-1,2-dicarbonitrile Chemical class [O-][N+](=O)C1=CC(C#N)=C(C#N)C=C1Br PZOBMISAMQBXIY-UHFFFAOYSA-N 0.000 claims abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract 2
- YEZSWHPLZBZVLH-UHFFFAOYSA-N Formylpyruvate Chemical class OC(=O)C(=O)CC=O YEZSWHPLZBZVLH-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
- 230000015572 biosynthetic process Effects 0.000 claims abstract 2
- 238000006243 chemical reaction Methods 0.000 claims abstract 2
- 230000003993 interaction Effects 0.000 claims abstract 2
- 238000000034 method Methods 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
- 238000003786 synthesis reaction Methods 0.000 claims abstract 2
- 0 *C(c1c(C(O*)=O)[o]c(cc2C#N)c1cc2C#N)=O Chemical compound *C(c1c(C(O*)=O)[o]c(cc2C#N)c1cc2C#N)=O 0.000 description 1
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- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Способ получения эфиров замещенных 5,6-дицианобензофуран-2-карбоновых кислот общей формулы ! ! где a R=4-Me-C6H4; b R=4-MeO-C6H4; c R=2-thienyl; R1=Me, Et, ! заключающийся в том, что в качестве исходных реагентов для синтеза эфиров замещенных 5,6-дицианобензофуран-2-карбоновых кислот используют 4-бром-5-нитрофталонитрил и натриевые соли производных 2,4-диоксобутановых кислот, взаимодействие указанных реагентов протекает при температуре 75…85°С и мольном соотношении 1:2 соответственно в течение 18-24 ч в растворе диметилформамида, затем реакционную массу разбавляют десятикратным избытком воды с Т=0…25°С, выделившийся смолистый осадок экстрагируют хлористым метиленом, тщательно промывают водой, хроматографируют на силикагеле, элюент (растворитель) упаривают, выпавший осадок отфильтровывают, перекристаллизовывают из спирта. A method of producing esters of substituted 5,6-dicyanobenzofuran-2-carboxylic acids of the general formula! ! where a R = 4-Me-C6H4; b R = 4-MeO-C6H4; c R = 2-thienyl; R1 = Me, Et,! consisting in the fact that as starting reagents for the synthesis of esters of substituted 5,6-dicyanobenzofuran-2-carboxylic acids, 4-bromo-5-nitrophthalonitrile and sodium salts of derivatives of 2,4-dioxobutanoic acids are used, the interaction of these reagents proceeds at a temperature of 75 ... 85 ° C and a molar ratio of 1: 2, respectively, for 18-24 hours in a solution of dimethylformamide, then the reaction mass is diluted with a ten-fold excess of water with T = 0 ... 25 ° C, the resulting resinous precipitate is extracted with methylene chloride, washed thoroughly with water, and atografiruyut on silica gel (solvent) is evaporated, the precipitate was filtered off and recrystallized from alcohol.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| RU2010120062/04A RU2446143C2 (en) | 2010-05-19 | 2010-05-19 | Method of producing ethers of substituted 5,6-dicyanobenzofuran-2-carboxylic acids |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| RU2010120062/04A RU2446143C2 (en) | 2010-05-19 | 2010-05-19 | Method of producing ethers of substituted 5,6-dicyanobenzofuran-2-carboxylic acids |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU2010120062A true RU2010120062A (en) | 2011-11-27 |
| RU2446143C2 RU2446143C2 (en) | 2012-03-27 |
Family
ID=45317587
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2010120062/04A RU2446143C2 (en) | 2010-05-19 | 2010-05-19 | Method of producing ethers of substituted 5,6-dicyanobenzofuran-2-carboxylic acids |
Country Status (1)
| Country | Link |
|---|---|
| RU (1) | RU2446143C2 (en) |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19514567A1 (en) * | 1995-04-20 | 1996-10-24 | Merck Patent Gmbh | Benzofurans |
| ATE229516T1 (en) * | 1996-08-19 | 2002-12-15 | Altana Pharma Ag | BENZOFURAN-4-CARBOXAMIDE |
| KR20070001259A (en) * | 2004-04-09 | 2007-01-03 | 아릭스 테라퓨틱스 | Benzofuranyl derivatives useful for the treatment of cardiac arrhythmias |
-
2010
- 2010-05-19 RU RU2010120062/04A patent/RU2446143C2/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| RU2446143C2 (en) | 2012-03-27 |
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| MM4A | The patent is invalid due to non-payment of fees |
Effective date: 20140520 |