CA1095056A - Process for the manufacture of isoxazole derivatives - Google Patents
Process for the manufacture of isoxazole derivativesInfo
- Publication number
- CA1095056A CA1095056A CA292,253A CA292253A CA1095056A CA 1095056 A CA1095056 A CA 1095056A CA 292253 A CA292253 A CA 292253A CA 1095056 A CA1095056 A CA 1095056A
- Authority
- CA
- Canada
- Prior art keywords
- fluorine
- formula
- carbon atoms
- represent
- chlorine
- 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
- 238000000034 method Methods 0.000 title claims abstract description 17
- 238000004519 manufacturing process Methods 0.000 title description 3
- 150000002545 isoxazoles Chemical class 0.000 title 1
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims abstract description 12
- ZYEWRBNSDKQNSJ-UHFFFAOYSA-N 5-methyl-n-phenyl-1,2-oxazole-4-carboxamide Chemical class O1N=CC(C(=O)NC=2C=CC=CC=2)=C1C ZYEWRBNSDKQNSJ-UHFFFAOYSA-N 0.000 claims abstract description 5
- 238000002360 preparation method Methods 0.000 claims abstract description 5
- AGQOIYCTCOEHGR-UHFFFAOYSA-N 5-methyl-1,2-oxazole Chemical class CC1=CC=NO1 AGQOIYCTCOEHGR-UHFFFAOYSA-N 0.000 claims abstract description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 24
- 229910052731 fluorine Inorganic materials 0.000 claims description 18
- 239000011737 fluorine Substances 0.000 claims description 18
- 239000000460 chlorine Substances 0.000 claims description 15
- 229910052801 chlorine Inorganic materials 0.000 claims description 15
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 14
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 13
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 13
- 229910052794 bromium Inorganic materials 0.000 claims description 13
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 11
- -1 methylenedioxy group Chemical group 0.000 claims description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 125000001153 fluoro group Chemical group F* 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 4
- 125000004414 alkyl thio group Chemical group 0.000 claims description 3
- 239000011230 binding agent Substances 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 125000001624 naphthyl group Chemical group 0.000 claims description 3
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 7
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- 239000012442 inert solvent Substances 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 5
- 230000000202 analgesic effect Effects 0.000 abstract description 2
- 239000002260 anti-inflammatory agent Substances 0.000 abstract description 2
- 230000001741 anti-phlogistic effect Effects 0.000 abstract description 2
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- KRZCOLNOCZKSDF-UHFFFAOYSA-N 4-fluoroaniline Chemical compound NC1=CC=C(F)C=C1 KRZCOLNOCZKSDF-UHFFFAOYSA-N 0.000 description 4
- VQBXUKGMJCPBMF-UHFFFAOYSA-N 5-methyl-1,2-oxazole-4-carboxylic acid Chemical class CC=1ON=CC=1C(O)=O VQBXUKGMJCPBMF-UHFFFAOYSA-N 0.000 description 4
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- HVTVCLGVPVGJPT-UHFFFAOYSA-N n-(4-fluorophenyl)-5-methyl-1,2-oxazole-4-carboxamide Chemical compound O1N=CC(C(=O)NC=2C=CC(F)=CC=2)=C1C HVTVCLGVPVGJPT-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- YLIAQPCKUPLGJA-UHFFFAOYSA-N (4-bromophenyl) 5-methyl-1,2-oxazole-4-carboxylate Chemical compound O1N=CC(C(=O)OC=2C=CC(Br)=CC=2)=C1C YLIAQPCKUPLGJA-UHFFFAOYSA-N 0.000 description 1
- ZSOSULCXAHAKEN-UHFFFAOYSA-N (5-methyl-1,2-oxazole-4-carbonyl) 5-methyl-1,2-oxazole-4-carboxylate Chemical class O1N=CC(C(=O)OC(=O)C2=C(ON=C2)C)=C1C ZSOSULCXAHAKEN-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 1
- ZKAQPVQEYCFRTK-UHFFFAOYSA-N 5-methyl-1,2-oxazole-4-carbonyl chloride Chemical compound CC=1ON=CC=1C(Cl)=O ZKAQPVQEYCFRTK-UHFFFAOYSA-N 0.000 description 1
- FWXFIRXCTXCWQR-UHFFFAOYSA-N CC(ON=C1)=C1C(NC(C=C1)=CC(F)=C1Cl)=O Chemical compound CC(ON=C1)=C1C(NC(C=C1)=CC(F)=C1Cl)=O FWXFIRXCTXCWQR-UHFFFAOYSA-N 0.000 description 1
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 1
- 206010013786 Dry skin Diseases 0.000 description 1
- UQVKBIUUAUHWQL-UHFFFAOYSA-N N-(3,4-difluorophenyl)-5-methyl-1,2-oxazole-4-carboxamide Chemical compound Cc1oncc1C(=O)Nc1ccc(F)c(F)c1 UQVKBIUUAUHWQL-UHFFFAOYSA-N 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- DYRDKSSFIWVSNM-UHFFFAOYSA-N acetoacetanilide Chemical compound CC(=O)CC(=O)NC1=CC=CC=C1 DYRDKSSFIWVSNM-UHFFFAOYSA-N 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910000272 alkali metal oxide Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 150000001718 carbodiimides Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- XPPNZYLHNQZKNO-UHFFFAOYSA-N ethoxycarbonyl 5-methyl-1,2-oxazole-4-carboxylate Chemical compound CC1=C(C=NO1)C(=O)OC(=O)OCC XPPNZYLHNQZKNO-UHFFFAOYSA-N 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- HHEMKQQXMOSUHA-UHFFFAOYSA-N n-(1,3-benzodioxol-5-yl)-5-methyl-1,2-oxazole-4-carboxamide Chemical compound O1N=CC(C(=O)NC=2C=C3OCOC3=CC=2)=C1C HHEMKQQXMOSUHA-UHFFFAOYSA-N 0.000 description 1
- RIFXXMYHOTWSEC-UHFFFAOYSA-N n-(3,4-dichlorophenyl)-5-methyl-1,2-oxazole-4-carboxamide Chemical compound O1N=CC(C(=O)NC=2C=C(Cl)C(Cl)=CC=2)=C1C RIFXXMYHOTWSEC-UHFFFAOYSA-N 0.000 description 1
- YMCOUKHPOVRSLB-UHFFFAOYSA-N n-(3-chloro-4-fluorophenyl)-5-methyl-1,2-oxazole-4-carboxamide Chemical compound O1N=CC(C(=O)NC=2C=C(Cl)C(F)=CC=2)=C1C YMCOUKHPOVRSLB-UHFFFAOYSA-N 0.000 description 1
- PUELKQSGLBILDA-UHFFFAOYSA-N n-(4-bromophenyl)-5-methyl-1,2-oxazole-4-carboxamide Chemical compound O1N=CC(C(=O)NC=2C=CC(Br)=CC=2)=C1C PUELKQSGLBILDA-UHFFFAOYSA-N 0.000 description 1
- NHJJLJQNBURBGT-UHFFFAOYSA-N n-(4-chlorophenyl)-5-methyl-1,2-oxazole-4-carboxamide Chemical compound O1N=CC(C(=O)NC=2C=CC(Cl)=CC=2)=C1C NHJJLJQNBURBGT-UHFFFAOYSA-N 0.000 description 1
- LTOIKBCWFOMQRB-UHFFFAOYSA-N n-(4-iodophenyl)-5-methyl-1,2-oxazole-4-carboxamide Chemical compound O1N=CC(C(=O)NC=2C=CC(I)=CC=2)=C1C LTOIKBCWFOMQRB-UHFFFAOYSA-N 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- LGVXPSMGABFXST-UHFFFAOYSA-N phenyl 5-methyl-1,2-oxazole-4-carboxylate Chemical compound C1(=CC=CC=C1)OC(=O)C=1C=NOC=1C LGVXPSMGABFXST-UHFFFAOYSA-N 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 238000003892 spreading Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
- C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
- C07D261/06—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
- C07D261/10—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D261/18—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19762654797 DE2654797A1 (de) | 1976-12-03 | 1976-12-03 | Verfahren zur herstellung von isoxazolderivaten |
| DEP2654797.7 | 1976-12-03 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1095056A true CA1095056A (en) | 1981-02-03 |
Family
ID=5994582
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA292,253A Expired CA1095056A (en) | 1976-12-03 | 1977-12-02 | Process for the manufacture of isoxazole derivatives |
Country Status (14)
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0035285A3 (en) * | 1979-08-17 | 1981-10-14 | American Cyanamid Company | Novel isoxazole carboxylic acid phenyl esters, pharmaceutical compositions containing certain of said esters, and process for preparing said esters |
| JPS55500866A (enrdf_load_stackoverflow) * | 1978-11-03 | 1980-10-30 | ||
| DE2854439A1 (de) * | 1978-12-16 | 1980-07-03 | Hoechst Ag | Ein isoxazolderivat, verfahren zu seiner herstellung, diese verbindung enthaltende mittel und verwendung |
| DE2854438A1 (de) * | 1978-12-16 | 1980-07-03 | Hoechst Ag | Isoxazolderivate, verfahren zu ihrer herstellung, diese verbindungen enthaltende mittel und ihre verwendung |
| ATE14724T1 (de) * | 1979-06-11 | 1985-08-15 | Ciba Geigy Ag | Alphacarbamoyl-pyrrolpropionitrile, verfahren zu ihrer herstellung, sowie pharmazeutische praeparate die diese verbindungen enthalten. |
| DE3247454A1 (de) * | 1982-12-22 | 1984-06-28 | Laboratorios Bago S.A., Buenos Aires | Substituierte 3-phenyl-5-methyl-isoxazol-4-carboxy-anilide, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
| GB8619432D0 (en) * | 1986-08-08 | 1986-09-17 | Lilly Industries Ltd | Pharmaceutical compounds |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES448386A1 (es) * | 1975-06-05 | 1978-04-16 | Hoechst Ag | Procedimiento para la preparacion de anilidas de acido 5-me-til-isoxazol-4-carboxilico. |
| DE2525023A1 (de) * | 1975-06-05 | 1976-12-16 | Hoechst Ag | Neue isoxazolderivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende fungizide |
-
1976
- 1976-12-03 DE DE19762654797 patent/DE2654797A1/de not_active Withdrawn
-
1977
- 1977-11-15 CH CH1393277A patent/CH609341A5/xx not_active IP Right Cessation
- 1977-11-28 ES ES464533A patent/ES464533A2/es not_active Expired
- 1977-11-28 NL NL7713083A patent/NL7713083A/xx not_active Application Discontinuation
- 1977-12-01 LU LU78614A patent/LU78614A1/xx unknown
- 1977-12-01 IT IT3028677A patent/IT1089430B/it active
- 1977-12-02 IE IE245377A patent/IE46001B1/en unknown
- 1977-12-02 FR FR7736424A patent/FR2381756A2/fr active Granted
- 1977-12-02 CA CA292,253A patent/CA1095056A/en not_active Expired
- 1977-12-02 DK DK538777A patent/DK538777A/da not_active Application Discontinuation
- 1977-12-02 AT AT866177A patent/AT361917B/de not_active IP Right Cessation
- 1977-12-02 GB GB5034277A patent/GB1572309A/en not_active Expired
- 1977-12-03 JP JP14561977A patent/JPS5371068A/ja active Pending
- 1977-12-05 BE BE183167A patent/BE861500R/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| AT361917B (de) | 1981-04-10 |
| NL7713083A (nl) | 1978-06-06 |
| CH609341A5 (en) | 1979-02-28 |
| LU78614A1 (enrdf_load_stackoverflow) | 1978-07-14 |
| JPS5371068A (en) | 1978-06-24 |
| IE46001B1 (en) | 1983-01-26 |
| ATA866177A (de) | 1980-09-15 |
| GB1572309A (en) | 1980-07-30 |
| ES464533A2 (es) | 1979-10-16 |
| FR2381756A2 (fr) | 1978-09-22 |
| DK538777A (da) | 1978-06-04 |
| IE46001L (en) | 1978-06-03 |
| BE861500R (fr) | 1978-06-05 |
| FR2381756B2 (enrdf_load_stackoverflow) | 1982-10-29 |
| IT1089430B (it) | 1985-06-18 |
| DE2654797A1 (de) | 1978-06-08 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |