KR890014456A - 플루페남산의 2-(2-히드록시에톡시)에탄올아민을 제조하는 방법 - Google Patents
플루페남산의 2-(2-히드록시에톡시)에탄올아민을 제조하는 방법 Download PDFInfo
- Publication number
- KR890014456A KR890014456A KR1019890003843A KR890003843A KR890014456A KR 890014456 A KR890014456 A KR 890014456A KR 1019890003843 A KR1019890003843 A KR 1019890003843A KR 890003843 A KR890003843 A KR 890003843A KR 890014456 A KR890014456 A KR 890014456A
- Authority
- KR
- South Korea
- Prior art keywords
- acid
- excess
- reaction mixture
- hydroxyethoxy
- diol
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 238000000034 method Methods 0.000 title claims 7
- LPEPZBJOKDYZAD-UHFFFAOYSA-N flufenamic acid Chemical compound OC(=O)C1=CC=CC=C1NC1=CC=CC(C(F)(F)F)=C1 LPEPZBJOKDYZAD-UHFFFAOYSA-N 0.000 title claims 5
- 229960004369 flufenamic acid Drugs 0.000 title claims 4
- 150000002009 diols Chemical class 0.000 claims 5
- 239000011541 reaction mixture Substances 0.000 claims 5
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims 4
- 150000002148 esters Chemical class 0.000 claims 4
- -1 2-hydroxyethoxy Chemical group 0.000 claims 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 3
- 239000002253 acid Substances 0.000 claims 3
- 238000006243 chemical reaction Methods 0.000 claims 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims 2
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 claims 2
- 239000007864 aqueous solution Substances 0.000 claims 2
- 239000003054 catalyst Substances 0.000 claims 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 2
- 239000004215 Carbon black (E152) Substances 0.000 claims 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims 1
- 238000003820 Medium-pressure liquid chromatography Methods 0.000 claims 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims 1
- 239000003377 acid catalyst Substances 0.000 claims 1
- 239000003463 adsorbent Substances 0.000 claims 1
- 239000008346 aqueous phase Substances 0.000 claims 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 claims 1
- 238000005886 esterification reaction Methods 0.000 claims 1
- 229930195733 hydrocarbon Natural products 0.000 claims 1
- 150000002430 hydrocarbons Chemical group 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000005825 oxyethoxy group Chemical group [H]C([H])(O[*:1])C([H])([H])O[*:2] 0.000 claims 1
- 239000000741 silica gel Substances 0.000 claims 1
- 229910002027 silica gel Inorganic materials 0.000 claims 1
- 239000007787 solid Substances 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/52—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
- C07C229/54—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton with amino and carboxyl groups bound to carbon atoms of the same non-condensed six-membered aromatic ring
- C07C229/56—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton with amino and carboxyl groups bound to carbon atoms of the same non-condensed six-membered aromatic ring with amino and carboxyl groups bound in ortho-position
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C227/14—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof
- C07C227/18—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof by reactions involving amino or carboxyl groups, e.g. hydrolysis of esters or amides, by formation of halides, salts or esters
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Description
Claims (7)
- (a) 산촉매의 존재하에서 100 내지 140℃, 바람직하게는 100 내지 120℃의 반응온도에서 플루페남산을 과잉의 2-(2-히드록시에톡시)에탄올과 직접 반응시키고, (b) 반응혼합물로부터 과잉의 디올을 제거하고, (c) 조에스테르를 처리함으로써 플로페남산(N-(α, α, α-트리플루오로-m-톨릴)안트라닐산)의 2-(2-히드록시에톡시)에탄올에스테르를 제조하는 방법에 있어서, 반응혼합물로부터 반응수를 동시 제거함이 없이 플루페남산 몰당 8 내지 15몰의 과잉의 디올로 반응을 행하는 것을 특징으로 하는 플루페남산의 2-(2-히드록시에톡시)에탄올에스테르를 제조하는 방법.
- 제1항에 있어서, 산몰당 0.25 내지 1몰의 촉매를 사용하는 것을 특징으로 하는 방법.
- 제1항에 있어서, 플루페남산 몰당 10.5 내지 12몰의 디올과잉량으로 반응을 행하는 것을 특징으로 하는 방법.
- 제1항 내지 제3항중의 어느 하나에 있어서, 에스테르화 반응의 종결후 과잉의 디올을 분리하기 위해 알칼리금속 수산화물 또는 알칼리토금속수산화물 또는그들의 탄산염의 수용액을 반응혼합물에 가하고, 그리하여 에스테르 조제품을 분리하고 과잉의 2-(2-히드록시에톡시)에탄올을 물층(수상)내로 이행하게 하는 것을 특징으로 하는 방법.
- 제1항 내지 제3항중의 어느 하나에 있어서, 과잉의 디올을 제거하기 위해 중화될 때까지 반응혼합물을 고형의 알칼리금속 수산화물 또는 알칼리토금속수산화물 또는 그들의 탄산염과 혼합시키고 이어서 조에스테르를 탄화수소용제, 바람직하게는 톨루엔으로 추출하는 것을 특징으로 하는 방법.
- 제1항 내지 제5항중의 어느 하나에 있어서, 통상의 흡착제 바람직하게는 실리카겔을 사용하여 10 내지 20바아의 압력에서 중간압력 액체크로마토그래피에 의해 조 에스테르제품을 정제하는 것을 특징으로 하는 방법.
- 제1항 내지 제6항중의 어느 하나에 있어서, 촉매가 p-톨루엔술폰산-1수염인 것을 특징으로 하는 방법.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DEP3811119,5 | 1988-03-31 | ||
DE3811119A DE3811119C1 (ko) | 1988-03-31 | 1988-03-31 | |
DEP3811119.5 | 1988-03-31 |
Publications (2)
Publication Number | Publication Date |
---|---|
KR890014456A true KR890014456A (ko) | 1989-10-23 |
KR950013472B1 KR950013472B1 (ko) | 1995-11-08 |
Family
ID=6351240
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
KR1019890003843A Expired - Fee Related KR950013472B1 (ko) | 1988-03-31 | 1989-03-27 | 플루페남산의 2-(2-히드록시에톡시)에탄올아민을 제조하는 방법 |
Country Status (9)
Country | Link |
---|---|
US (1) | US4980498A (ko) |
EP (1) | EP0336146B1 (ko) |
JP (1) | JPH029850A (ko) |
KR (1) | KR950013472B1 (ko) |
AT (1) | ATE92911T1 (ko) |
CA (1) | CA1307538C (ko) |
DE (2) | DE3811119C1 (ko) |
ES (1) | ES2042834T3 (ko) |
FI (1) | FI90659C (ko) |
Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2578749Y2 (ja) * | 1991-10-28 | 1998-08-13 | 株式会社日本フォトサイエンス | 液体の光化学反応処理装置 |
US5595813A (en) * | 1992-09-22 | 1997-01-21 | Takenaka Corporation | Architectural material using metal oxide exhibiting photocatalytic activity |
JP2568157Y2 (ja) * | 1993-05-31 | 1998-04-08 | 水青工業株式会社 | 吐水口および浄水器 |
US6106955A (en) * | 1997-01-14 | 2000-08-22 | Takenaka Corporation | Metal material having photocatalytic activity and method of manufacturing the same |
CA3115048C (en) | 2018-09-28 | 2024-02-13 | Griffith University | Agents and methods for modulating pathogen activity using ligands of complement receptor 3 |
Family Cites Families (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CA726767A (en) * | 1966-01-25 | Parke, Davis And Company | Anthranilic acid esters and methods for producing same | |
CA904340A (en) * | 1972-07-04 | Boltze Karl-Heinz | Esters of substituted anthranilic acid | |
DE1939111C3 (de) * | 1969-08-01 | 1974-04-18 | Troponwerke Dinklage & Co, 5000 Koeln | Derivate der N- eckige Klammer auf 3-Trifluormethylphenyl eckige Klammer zu -anthranilsäure, Verfahren zu ihrer Herstellung und pharmakologisch wirksame Zubereitungen derselben |
DE1939112C3 (de) * | 1969-08-01 | 1975-03-06 | Troponwerke Dinklage & Co, 5000 Koeln | Ester der N-(3-Trifluormethylphenyl) -anthranilsäure, Verfahren zu ihrer Herstellung und pharmakologisch wirksame Zubereitungen derselben |
JPS53105445A (en) * | 1977-02-26 | 1978-09-13 | Hokuriku Pharmaceutical | Nn*33trifluoromethylphenyl* anthranylate alklyester derivative and process for preparing same |
JPS543032A (en) * | 1977-06-06 | 1979-01-11 | Hokuriku Pharmaceutical | Furphenamicester derivative and process for preparing same |
DE2834170C2 (de) * | 1978-08-04 | 1984-02-23 | Troponwerke GmbH & Co KG, 5000 Köln | Verfahren zur Herstellung von 2-(2-Hydroxyäthoxy)äthyl-N-(α,α,α-trifluor-m-tolyl)anthranilat |
DE2834167C2 (de) * | 1978-08-04 | 1984-01-26 | Troponwerke GmbH & Co KG, 5000 Köln | Verfahren zur Herstellung von 2-(2-Hydroxyäthoxy)äthyl-N-(α,α,α-trifluor-m-tolyl)anthranilat |
JPS58148840A (ja) * | 1982-03-01 | 1983-09-05 | Dainippon Pharmaceut Co Ltd | N−(α,α,α−トリフルオロ−m−トリル)アントラニル酸2−(2−ヒドロキシエトキシ)エチルエステルの製法 |
KR840009066A (ko) * | 1983-03-24 | 1984-12-24 | 베르너 쇤, 게르트 바디케 | 에토 페나메이트의 정제방법 |
-
1988
- 1988-03-31 DE DE3811119A patent/DE3811119C1/de not_active Expired
-
1989
- 1989-03-14 DE DE8989104495T patent/DE58905205D1/de not_active Expired - Fee Related
- 1989-03-14 EP EP89104495A patent/EP0336146B1/de not_active Expired - Lifetime
- 1989-03-14 AT AT89104495T patent/ATE92911T1/de not_active IP Right Cessation
- 1989-03-14 ES ES89104495T patent/ES2042834T3/es not_active Expired - Lifetime
- 1989-03-23 FI FI891410A patent/FI90659C/fi not_active IP Right Cessation
- 1989-03-27 KR KR1019890003843A patent/KR950013472B1/ko not_active Expired - Fee Related
- 1989-03-30 JP JP1076845A patent/JPH029850A/ja active Pending
- 1989-03-30 CA CA000595220A patent/CA1307538C/en not_active Expired - Lifetime
- 1989-03-31 US US07/331,125 patent/US4980498A/en not_active Expired - Fee Related
Also Published As
Publication number | Publication date |
---|---|
EP0336146B1 (de) | 1993-08-11 |
DE3811119C1 (ko) | 1989-10-12 |
DE58905205D1 (de) | 1993-09-16 |
FI90659B (fi) | 1993-11-30 |
US4980498A (en) | 1990-12-25 |
FI90659C (fi) | 1994-03-10 |
EP0336146A3 (de) | 1991-03-27 |
EP0336146A2 (de) | 1989-10-11 |
KR950013472B1 (ko) | 1995-11-08 |
CA1307538C (en) | 1992-09-15 |
ATE92911T1 (de) | 1993-08-15 |
ES2042834T3 (es) | 1993-12-16 |
FI891410L (fi) | 1989-10-01 |
FI891410A0 (fi) | 1989-03-23 |
JPH029850A (ja) | 1990-01-12 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
PA0109 | Patent application |
Patent event code: PA01091R01D Comment text: Patent Application Patent event date: 19890327 |
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PG1501 | Laying open of application | ||
A201 | Request for examination | ||
PA0201 | Request for examination |
Patent event code: PA02012R01D Patent event date: 19921202 Comment text: Request for Examination of Application Patent event code: PA02011R01I Patent event date: 19890327 Comment text: Patent Application |
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E902 | Notification of reason for refusal | ||
PE0902 | Notice of grounds for rejection |
Comment text: Notification of reason for refusal Patent event date: 19950731 Patent event code: PE09021S01D |
|
G160 | Decision to publish patent application | ||
PG1605 | Publication of application before grant of patent |
Comment text: Decision on Publication of Application Patent event code: PG16051S01I Patent event date: 19951012 |
|
E701 | Decision to grant or registration of patent right | ||
PE0701 | Decision of registration |
Patent event code: PE07011S01D Comment text: Decision to Grant Registration Patent event date: 19960207 |
|
GRNT | Written decision to grant | ||
PR0701 | Registration of establishment |
Comment text: Registration of Establishment Patent event date: 19960507 Patent event code: PR07011E01D |
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PR1002 | Payment of registration fee |
Payment date: 19960507 End annual number: 3 Start annual number: 1 |
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LAPS | Lapse due to unpaid annual fee | ||
PC1903 | Unpaid annual fee |