CS255045B1 - N-(2,6-dichlorophenyl)-benziminophenylether - Google Patents
N-(2,6-dichlorophenyl)-benziminophenylether Download PDFInfo
- Publication number
- CS255045B1 CS255045B1 CS866327A CS632786A CS255045B1 CS 255045 B1 CS255045 B1 CS 255045B1 CS 866327 A CS866327 A CS 866327A CS 632786 A CS632786 A CS 632786A CS 255045 B1 CS255045 B1 CS 255045B1
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- dichlorophenyl
- ether
- benziminophenyl
- benziminophenylether
- reaction mixture
- Prior art date
Links
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 12
- -1 2,6-dichlorophenyl Chemical group 0.000 claims abstract description 8
- 238000002360 preparation method Methods 0.000 abstract description 3
- 108010087765 Antipain Proteins 0.000 abstract description 2
- 230000003110 anti-inflammatory effect Effects 0.000 abstract description 2
- SDNYTAYICBFYFH-TUFLPTIASA-N antipain Chemical compound NC(N)=NCCC[C@@H](C=O)NC(=O)[C@H](C(C)C)NC(=O)[C@H](CCCN=C(N)N)NC(=O)N[C@H](C(O)=O)CC1=CC=CC=C1 SDNYTAYICBFYFH-TUFLPTIASA-N 0.000 abstract description 2
- 229940079593 drug Drugs 0.000 abstract description 2
- 239000003814 drug Substances 0.000 abstract description 2
- 159000000000 sodium salts Chemical class 0.000 abstract description 2
- 230000000857 drug effect Effects 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- ZTTZFKKSDSDFRF-UHFFFAOYSA-N N-(2,6-dichlorophenyl)benzenecarboximidoyl chloride Chemical compound C=1C=CC=CC=1C(Cl)=NC1=C(Cl)C=CC=C1Cl ZTTZFKKSDSDFRF-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- DCOPUUMXTXDBNB-UHFFFAOYSA-N diclofenac Chemical compound OC(=O)CC1=CC=CC=C1NC1=C(Cl)C=CC=C1Cl DCOPUUMXTXDBNB-UHFFFAOYSA-N 0.000 description 1
- 229960001193 diclofenac sodium Drugs 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229940031826 phenolate Drugs 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- ZGJADVGJIVEEGF-UHFFFAOYSA-M potassium;phenoxide Chemical group [K+].[O-]C1=CC=CC=C1 ZGJADVGJIVEEGF-UHFFFAOYSA-M 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- JGMJQSFLQWGYMQ-UHFFFAOYSA-M sodium;2,6-dichloro-n-phenylaniline;acetate Chemical compound [Na+].CC([O-])=O.ClC1=CC=CC(Cl)=C1NC1=CC=CC=C1 JGMJQSFLQWGYMQ-UHFFFAOYSA-M 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Řešení se týká N-(2,6-dichlorfenyl)- -benziminofenyletheru, který slouží jako meziprodukt pro přípravu sodné soli diclofenaou, která je žádaným léčivem s protibolestivým a protizánětlivým účinkem.The solution relates to N- (2,6-dichlorophenyl) - -benziminophenyl ether, which serves as a an intermediate for the preparation of the sodium salt of diclofenene, which is the desired anti-pain drug and anti-inflammatory effect.
Description
který je meziproduktem přípravy o-(2,6-dichloranilino)-fenyloctové kyseliny, jejíž sodné sůl (diclofenac natrium) je rozšířeným léčivem s protibolestivým a protizánětlivým účinkem.which is an intermediate for the preparation of o- (2,6-dichloroanilino) -phenylacetic acid, whose sodium salt (diclofenac sodium) is a widespread drug with an anti-pain and anti-inflammatory effect.
Nová sloučenina vzorce I se připravuje reakcí N-(2,6-dichlorfenyl)-benzimidoylchloridu s fenolétem alkalického kovu v prostředí protofilního rozpouštědla (alifatické ethery nebo estery alifatických kyselin), v rozmezí teplot 10°až 90°Cj zředěním reakční směsi vodou, separací organické fáze a odpařením rozpouštědla se získá surový N-(2,6-dichlorfenyl)-benziminofenylether jako žlutý viskózni, stáním krystalující olej. Krystalizací surového produktu z petroletheru se získá čistý N-(2,6-dichlorfenyl)-benziminofenylether, čistoty 99 %-ní (stanoveno plynovou chromatografií), ve formě žluté krystalické látky t.t. 7O,5°až 71,0°C.The novel compound of formula (I) is prepared by reacting N- (2,6-dichlorophenyl) -benzimidoyl chloride with an alkali metal phenolate in a protophilic solvent medium (aliphatic ethers or esters of aliphatic acids), between 10 ° and 90 ° C by diluting the reaction mixture with water, separating the organic phase and evaporation of the solvent gave crude N- (2,6-dichlorophenyl) -benziminophenyl ether as a yellow viscous, crystalline oil on standing. Crystallization of the crude product from petroleum ether gave pure N- (2,6-dichlorophenyl) -benziminophenyl ether, purity 99% (determined by gas chromatography), as a yellow crystalline solid, m.p. 70.5 ° to 71.0 ° C.
Následující příklad přípravy sloučeniny podle vynálezu látku pouze dokládá ale neomezuje.The following example illustrates the preparation of a compound of the invention but does not limit it.
PříkladExample
K suspensi 13,3 g (0,10 molu) fenolétu draselného ve 20 ml me255 045 thanolu se za stálého míchání a chlazení vodní lázní přidá roztok 28,5 g 0,10 molu N-(2,6-diehlorfenyí)-benzimidoylchloridu v 30 ml octanu ethylnatého tak, aby teplota reakční směsi byla udržována v rozmezí 30 až 40 C; po odeznění exothermní reakce se míchaná reakční směs vyhřeje na 50°C a udržováním této teploty po dobu 3 hod. se dosáhne proreagovéní obou komponent. Reakční směs, ochlazené na laboratorní teplotu, se zředí 70 ml octanu ethylnatého a protřepéním dest. vodou (β x 30 ml) se odstání anorganické soli a zbytky nezreagovaného fenolátu draselného; organická fáze, vysušená síranem sodným, se zbaví rozpouštědla destilací za sníženého tlaku. Získá se 25,0 g tj. 73,0 % th. olejovítého produktu, který stáním postupně zkrystaluje. Krystalizací z hexanu se získá 20 g N(2,6-dichlorfenyl)-benziminofenyletheru čistoty 98,5 %-ní jako žluté krystalické látky t.t. 7O,5°až 71°C.To a suspension of 13.3 g (0.10 mole) of potassium phenoleate in 20 ml of me255 045 thanol is added, while stirring and cooling in a water bath, a solution of 28.5 g of 0.10 mole of N- (2,6-dichlorophenyl) benzimidoyl chloride in 30 ml of ethyl acetate such that the temperature of the reaction mixture is maintained between 30 and 40 ° C; after the exothermic reaction subsided, the stirred reaction mixture was heated to 50 ° C and maintained at this temperature for 3 hours to produce a pro-reaction of both components. The reaction mixture, cooled to room temperature, was diluted with 70 ml of ethyl acetate and shaken with dest. water (β x 30 ml) leaves inorganic salts and unreacted potassium phenolate residues; the organic phase, dried over sodium sulfate, is freed from the solvent by distillation under reduced pressure. 25.0 g, i.e. 73.0% of th, is obtained. an oily product which gradually crystallizes on standing. Crystallization from hexane gave 20 g of N (2,6-dichlorophenyl) -benziminophenyl ether of purity 98.5% as a yellow crystalline solid, m.p. 70.5 ° -71 ° C.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS866327A CS255045B1 (en) | 1986-09-01 | 1986-09-01 | N-(2,6-dichlorophenyl)-benziminophenylether |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS866327A CS255045B1 (en) | 1986-09-01 | 1986-09-01 | N-(2,6-dichlorophenyl)-benziminophenylether |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CS632786A1 CS632786A1 (en) | 1987-06-11 |
| CS255045B1 true CS255045B1 (en) | 1988-02-15 |
Family
ID=5410054
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS866327A CS255045B1 (en) | 1986-09-01 | 1986-09-01 | N-(2,6-dichlorophenyl)-benziminophenylether |
Country Status (1)
| Country | Link |
|---|---|
| CS (1) | CS255045B1 (en) |
-
1986
- 1986-09-01 CS CS866327A patent/CS255045B1/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CS632786A1 (en) | 1987-06-11 |
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