CA1050565A - Process for preparing o-(2,6-dichloroanilino) phenylacetic acid and salts thereof - Google Patents
Process for preparing o-(2,6-dichloroanilino) phenylacetic acid and salts thereofInfo
- Publication number
- CA1050565A CA1050565A CA249,128A CA249128A CA1050565A CA 1050565 A CA1050565 A CA 1050565A CA 249128 A CA249128 A CA 249128A CA 1050565 A CA1050565 A CA 1050565A
- Authority
- CA
- Canada
- Prior art keywords
- process according
- hydrogen
- group
- hydrolysis
- compound
- 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.)
- Expired
Links
- DCOPUUMXTXDBNB-UHFFFAOYSA-N diclofenac Chemical compound OC(=O)CC1=CC=CC=C1NC1=C(Cl)C=CC=C1Cl DCOPUUMXTXDBNB-UHFFFAOYSA-N 0.000 title claims abstract description 7
- 150000003839 salts Chemical class 0.000 title claims description 7
- 238000004519 manufacturing process Methods 0.000 title description 2
- 238000006816 Chapman rearrangement reaction Methods 0.000 claims abstract description 10
- 230000003301 hydrolyzing effect Effects 0.000 claims abstract description 5
- 238000000034 method Methods 0.000 claims description 63
- 150000001875 compounds Chemical class 0.000 claims description 25
- 239000000460 chlorine Substances 0.000 claims description 24
- 230000007062 hydrolysis Effects 0.000 claims description 22
- 238000006460 hydrolysis reaction Methods 0.000 claims description 22
- -1 t-butoxy group Chemical group 0.000 claims description 20
- 229910052739 hydrogen Inorganic materials 0.000 claims description 17
- 239000001257 hydrogen Substances 0.000 claims description 17
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 15
- 238000002360 preparation method Methods 0.000 claims description 14
- 239000002904 solvent Substances 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 8
- 229910052801 chlorine Inorganic materials 0.000 claims description 7
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 239000012298 atmosphere Substances 0.000 claims description 3
- 239000012429 reaction media Substances 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims 6
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 2
- 238000005904 alkaline hydrolysis reaction Methods 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 2
- 229910052794 bromium Chemical group 0.000 claims 2
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims 2
- 229910052736 halogen Inorganic materials 0.000 claims 2
- 150000002367 halogens Chemical class 0.000 claims 2
- 150000002431 hydrogen Chemical class 0.000 claims 2
- 238000002955 isolation Methods 0.000 claims 1
- 239000000463 material Substances 0.000 abstract description 23
- KXDAEFPNCMNJSK-UHFFFAOYSA-M benzenecarboximidate Chemical compound [NH-]C(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-M 0.000 abstract description 5
- HOLHYSJJBXSLMV-UHFFFAOYSA-N 2,6-dichlorophenol Chemical compound OC1=C(Cl)C=CC=C1Cl HOLHYSJJBXSLMV-UHFFFAOYSA-N 0.000 abstract description 3
- 230000003110 anti-inflammatory effect Effects 0.000 abstract description 2
- 230000000202 analgesic effect Effects 0.000 abstract 1
- IAHMNSCQDXESII-UHFFFAOYSA-N benzenecarboximidoyl chloride Chemical compound ClC(=N)C1=CC=CC=C1 IAHMNSCQDXESII-UHFFFAOYSA-N 0.000 abstract 1
- 229960001259 diclofenac Drugs 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- DULCUDSUACXJJC-UHFFFAOYSA-N Ethyl phenylacetate Chemical compound CCOC(=O)CC1=CC=CC=C1 DULCUDSUACXJJC-UHFFFAOYSA-N 0.000 description 17
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 16
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 16
- 239000000047 product Substances 0.000 description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
- 239000012299 nitrogen atmosphere Substances 0.000 description 13
- 230000008707 rearrangement Effects 0.000 description 13
- 238000006243 chemical reaction Methods 0.000 description 12
- 239000000126 substance Substances 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
- 239000000843 powder Substances 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical class CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000013078 crystal Substances 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- 238000010992 reflux Methods 0.000 description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 6
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 5
- KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 125000001424 substituent group Chemical group 0.000 description 5
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- 125000005843 halogen group Chemical group 0.000 description 4
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- 150000003936 benzamides Chemical class 0.000 description 3
- 239000010410 layer Substances 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- SUSQOBVLVYHIEX-UHFFFAOYSA-N phenylacetonitrile Chemical compound N#CCC1=CC=CC=C1 SUSQOBVLVYHIEX-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical class [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 2
- MXMOTZIXVICDSD-UHFFFAOYSA-N anisoyl chloride Chemical compound COC1=CC=C(C(Cl)=O)C=C1 MXMOTZIXVICDSD-UHFFFAOYSA-N 0.000 description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 230000001276 controlling effect Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- ZWJINEZUASEZBH-UHFFFAOYSA-N fenamic acid Chemical class OC(=O)C1=CC=CC=C1NC1=CC=CC=C1 ZWJINEZUASEZBH-UHFFFAOYSA-N 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 229960003424 phenylacetic acid Drugs 0.000 description 2
- 239000003279 phenylacetic acid Substances 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- PEVXLUBJSVBZOI-UHFFFAOYSA-N 2-[2-(n-benzoyl-2,6-dichloroanilino)phenyl]acetic acid Chemical compound OC(=O)CC1=CC=CC=C1N(C=1C(=CC=CC=1Cl)Cl)C(=O)C1=CC=CC=C1 PEVXLUBJSVBZOI-UHFFFAOYSA-N 0.000 description 1
- SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- WZKSXHQDXQKIQJ-UHFFFAOYSA-N F[C](F)F Chemical compound F[C](F)F WZKSXHQDXQKIQJ-UHFFFAOYSA-N 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000001589 carboacyl group Chemical group 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- JEVCWSUVFOYBFI-UHFFFAOYSA-N cyanyl Chemical compound N#[C] JEVCWSUVFOYBFI-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- UELJXCRPLCATAK-UHFFFAOYSA-N ethyl 2-(2-aminophenyl)acetate Chemical compound CCOC(=O)CC1=CC=CC=C1N UELJXCRPLCATAK-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N hydrochloric acid Substances Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 238000007327 hydrogenolysis reaction Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- RGLJWQDZRQUITM-UHFFFAOYSA-N n-[2-(cyanomethyl)phenyl]-n-(2,6-dichlorophenyl)benzamide Chemical compound ClC1=CC=CC(Cl)=C1N(C=1C(=CC=CC=1)CC#N)C(=O)C1=CC=CC=C1 RGLJWQDZRQUITM-UHFFFAOYSA-N 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000006462 rearrangement reaction Methods 0.000 description 1
- 238000003385 ring cleavage reaction Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
Classifications
-
- 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
- C07C227/12—Formation of amino and carboxyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
-
- 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
- C07C229/40—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino groups bound to carbon atoms of at least one six-membered aromatic ring and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C229/42—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino groups bound to carbon atoms of at least one six-membered aromatic ring and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton with carboxyl groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by saturated carbon chains
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP50038682A JPS51113842A (en) | 1975-03-31 | 1975-03-31 | Process for preparing o-(2,6-dichloroanilino)phenyl acetic acid |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1050565A true CA1050565A (en) | 1979-03-13 |
Family
ID=12532044
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA249,128A Expired CA1050565A (en) | 1975-03-31 | 1976-03-30 | Process for preparing o-(2,6-dichloroanilino) phenylacetic acid and salts thereof |
Country Status (13)
| Country | Link |
|---|---|
| JP (1) | JPS51113842A (enExample) |
| AU (1) | AU504223B2 (enExample) |
| CA (1) | CA1050565A (enExample) |
| CH (1) | CH610877A5 (enExample) |
| DE (1) | DE2613838A1 (enExample) |
| DK (1) | DK157576A (enExample) |
| FI (1) | FI760842A7 (enExample) |
| FR (1) | FR2306196A1 (enExample) |
| GB (1) | GB1532087A (enExample) |
| GR (1) | GR59322B (enExample) |
| NL (1) | NL7603348A (enExample) |
| NO (1) | NO144667C (enExample) |
| SE (1) | SE413314B (enExample) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5815940A (ja) | 1981-07-23 | 1983-01-29 | Eisai Co Ltd | ポリプレニル系化合物およびその製造方法ならびにそれを含有する医薬 |
| EP0380712B1 (de) * | 1989-01-27 | 1995-01-04 | HEUMANN PHARMA GMBH & CO | Verfahren zur Herstellung von 2,6-Dichlordiphenylaminessigsäurederivaten |
| CN108947861A (zh) * | 2018-08-17 | 2018-12-07 | 复旦大学 | 双氯芬酸钠的合成方法 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1053269A (enExample) * | 1964-11-27 |
-
1975
- 1975-03-31 JP JP50038682A patent/JPS51113842A/ja active Granted
-
1976
- 1976-03-25 AU AU12370/76A patent/AU504223B2/en not_active Expired
- 1976-03-26 GR GR50400A patent/GR59322B/el unknown
- 1976-03-26 GB GB12175/76A patent/GB1532087A/en not_active Expired
- 1976-03-26 CH CH379076A patent/CH610877A5/xx not_active IP Right Cessation
- 1976-03-30 CA CA249,128A patent/CA1050565A/en not_active Expired
- 1976-03-30 SE SE7603779A patent/SE413314B/xx unknown
- 1976-03-30 NO NO761097A patent/NO144667C/no unknown
- 1976-03-30 FI FI760842A patent/FI760842A7/fi not_active Application Discontinuation
- 1976-03-31 NL NL7603348A patent/NL7603348A/xx not_active Application Discontinuation
- 1976-03-31 FR FR7609273A patent/FR2306196A1/fr active Granted
- 1976-03-31 DE DE19762613838 patent/DE2613838A1/de not_active Withdrawn
- 1976-03-31 DK DK157576A patent/DK157576A/da not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| NO144667B (no) | 1981-07-06 |
| NL7603348A (nl) | 1976-10-04 |
| GR59322B (en) | 1977-12-13 |
| FR2306196B1 (enExample) | 1979-06-29 |
| DK157576A (da) | 1976-10-01 |
| GB1532087A (en) | 1978-11-15 |
| FR2306196A1 (fr) | 1976-10-29 |
| AU1237076A (en) | 1977-09-29 |
| FI760842A7 (enExample) | 1976-10-01 |
| DE2613838A1 (de) | 1976-10-07 |
| AU504223B2 (en) | 1979-10-04 |
| JPS565218B2 (enExample) | 1981-02-04 |
| NO761097L (enExample) | 1976-10-01 |
| NO144667C (no) | 1981-10-14 |
| JPS51113842A (en) | 1976-10-07 |
| SE413314B (sv) | 1980-05-19 |
| SE7603779L (sv) | 1976-10-01 |
| CH610877A5 (en) | 1979-05-15 |
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