CA2336310A1 - Method for preparing 1-alkyl-pyrazol-5-carboxylic acid esters - Google Patents
Method for preparing 1-alkyl-pyrazol-5-carboxylic acid esters Download PDFInfo
- Publication number
- CA2336310A1 CA2336310A1 CA002336310A CA2336310A CA2336310A1 CA 2336310 A1 CA2336310 A1 CA 2336310A1 CA 002336310 A CA002336310 A CA 002336310A CA 2336310 A CA2336310 A CA 2336310A CA 2336310 A1 CA2336310 A1 CA 2336310A1
- Authority
- CA
- Canada
- Prior art keywords
- formula
- alkyl
- iii
- reaction
- branched
- 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.)
- Abandoned
Links
- 238000000034 method Methods 0.000 title claims abstract description 20
- 150000002148 esters Chemical class 0.000 claims abstract description 31
- 150000003839 salts Chemical class 0.000 claims abstract description 27
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 19
- 239000002904 solvent Substances 0.000 claims abstract description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 25
- 238000006243 chemical reaction Methods 0.000 claims description 25
- 239000000243 solution Substances 0.000 claims description 14
- 150000004703 alkoxides Chemical class 0.000 claims description 13
- 239000011541 reaction mixture Substances 0.000 claims description 10
- 238000002360 preparation method Methods 0.000 claims description 9
- 150000001450 anions Chemical class 0.000 claims description 7
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group 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 claims description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 6
- 229910052708 sodium Inorganic materials 0.000 claims description 6
- 239000011734 sodium Chemical group 0.000 claims description 6
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 5
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical group [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 5
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical group [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 5
- 239000007864 aqueous solution Substances 0.000 claims description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
- 229910052744 lithium Inorganic materials 0.000 claims description 5
- 229910052749 magnesium Chemical group 0.000 claims description 5
- 239000011777 magnesium Chemical group 0.000 claims description 5
- 150000007524 organic acids Chemical class 0.000 claims description 5
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 4
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical group [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 4
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric Acid Chemical compound [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 claims description 4
- 125000004429 atom Chemical group 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 4
- 150000002576 ketones Chemical class 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 229910052751 metal Inorganic materials 0.000 claims description 4
- 239000002184 metal Substances 0.000 claims description 4
- 229910052700 potassium Inorganic materials 0.000 claims description 4
- 239000011591 potassium Chemical group 0.000 claims description 4
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 3
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 2
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 claims description 2
- QISOBCMNUJQOJU-UHFFFAOYSA-N 4-bromo-1h-pyrazole-5-carboxylic acid Chemical compound OC(=O)C=1NN=CC=1Br QISOBCMNUJQOJU-UHFFFAOYSA-N 0.000 claims description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical group [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Natural products OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 2
- 229910017849 NH2—NH2 Inorganic materials 0.000 claims description 2
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 claims description 2
- 229910052791 calcium Inorganic materials 0.000 claims description 2
- 239000011575 calcium Chemical group 0.000 claims description 2
- 235000015165 citric acid Nutrition 0.000 claims description 2
- 239000001530 fumaric acid Substances 0.000 claims description 2
- 239000001630 malic acid Substances 0.000 claims description 2
- 235000011090 malic acid Nutrition 0.000 claims description 2
- 230000035484 reaction time Effects 0.000 claims description 2
- 235000002906 tartaric acid Nutrition 0.000 claims description 2
- 239000011975 tartaric acid Substances 0.000 claims description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims 3
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims 2
- HFVMEOPYDLEHBR-UHFFFAOYSA-N (2-fluorophenyl)-phenylmethanol Chemical compound C=1C=CC=C(F)C=1C(O)C1=CC=CC=C1 HFVMEOPYDLEHBR-UHFFFAOYSA-N 0.000 claims 1
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 claims 1
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims 1
- 239000001361 adipic acid Substances 0.000 claims 1
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 claims 1
- 150000001735 carboxylic acids Chemical class 0.000 claims 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims 1
- 239000011976 maleic acid Substances 0.000 claims 1
- 239000002253 acid Substances 0.000 abstract description 8
- 230000015572 biosynthetic process Effects 0.000 abstract description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 10
- 239000000203 mixture Substances 0.000 description 9
- -1 triethyloxonium tetrafluoroborate Chemical compound 0.000 description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- HDZGCSFEDULWCS-UHFFFAOYSA-N monomethylhydrazine Chemical compound CNN HDZGCSFEDULWCS-UHFFFAOYSA-N 0.000 description 4
- XNLICIUVMPYHGG-UHFFFAOYSA-N pentan-2-one Chemical compound CCCC(C)=O XNLICIUVMPYHGG-UHFFFAOYSA-N 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 3
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 3
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000001476 alcoholic effect Effects 0.000 description 3
- FXEBKHIHECCEFH-UHFFFAOYSA-N amino(methyl)azanium;formate Chemical compound C[NH2+]N.[O-]C=O FXEBKHIHECCEFH-UHFFFAOYSA-N 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 3
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 230000029936 alkylation Effects 0.000 description 2
- 238000005804 alkylation reaction Methods 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- DMAUJRWSYKLVHX-UHFFFAOYSA-N ethyl 2,4-dioxoheptanoate Chemical compound CCCC(=O)CC(=O)C(=O)OCC DMAUJRWSYKLVHX-UHFFFAOYSA-N 0.000 description 2
- SSOOGSMECVGPOT-UHFFFAOYSA-N ethyl 3,5-dioxohexanoate Chemical compound CCOC(=O)CC(=O)CC(C)=O SSOOGSMECVGPOT-UHFFFAOYSA-N 0.000 description 2
- NVHCOTWQOUIBQN-UHFFFAOYSA-N ethyl 3,5-dioxooctanoate Chemical compound CCCC(=O)CC(=O)CC(=O)OCC NVHCOTWQOUIBQN-UHFFFAOYSA-N 0.000 description 2
- SUALHSUMUQQLJP-UHFFFAOYSA-N ethyl 5-propyl-1h-pyrazole-3-carboxylate Chemical compound CCCC1=CC(C(=O)OCC)=NN1 SUALHSUMUQQLJP-UHFFFAOYSA-N 0.000 description 2
- 150000002429 hydrazines Chemical class 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 239000012266 salt solution Substances 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 2
- PXRXGHUTKHXUGF-UHFFFAOYSA-N 1,5-dimethylpyrazole-3-carboxylic acid Chemical compound CC1=CC(C(O)=O)=NN1C PXRXGHUTKHXUGF-UHFFFAOYSA-N 0.000 description 1
- KOPFEFZSAMLEHK-UHFFFAOYSA-N 1h-pyrazole-5-carboxylic acid Chemical class OC(=O)C=1C=CNN=1 KOPFEFZSAMLEHK-UHFFFAOYSA-N 0.000 description 1
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 1
- UQFQONCQIQEYPJ-UHFFFAOYSA-N N-methylpyrazole Chemical class CN1C=CC=N1 UQFQONCQIQEYPJ-UHFFFAOYSA-N 0.000 description 1
- 230000000895 acaricidal effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 239000002168 alkylating agent Substances 0.000 description 1
- 229940100198 alkylating agent Drugs 0.000 description 1
- WIRPVVDZSMUIQF-UHFFFAOYSA-N amino(ethyl)azanium;formate Chemical compound [O-]C=O.CC[NH2+]N WIRPVVDZSMUIQF-UHFFFAOYSA-N 0.000 description 1
- GQBSPPLVFBNBHK-UHFFFAOYSA-N amino(propyl)azanium;formate Chemical compound [O-]C=O.CCC[NH2+]N GQBSPPLVFBNBHK-UHFFFAOYSA-N 0.000 description 1
- NHOWLEZFTHYCTP-UHFFFAOYSA-N benzylhydrazine Chemical group NNCC1=CC=CC=C1 NHOWLEZFTHYCTP-UHFFFAOYSA-N 0.000 description 1
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 1
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 150000008050 dialkyl sulfates Chemical class 0.000 description 1
- WYACBZDAHNBPPB-UHFFFAOYSA-N diethyl oxalate Chemical compound CCOC(=O)C(=O)OCC WYACBZDAHNBPPB-UHFFFAOYSA-N 0.000 description 1
- 238000007700 distillative separation Methods 0.000 description 1
- 150000002085 enols Chemical class 0.000 description 1
- UMXRSKKACFNPNO-UHFFFAOYSA-N ethyl 1-ethyl-5-methylpyrazole-3-carboxylate Chemical compound CCOC(=O)C=1C=C(C)N(CC)N=1 UMXRSKKACFNPNO-UHFFFAOYSA-N 0.000 description 1
- NTZFLNAMFHICLK-UHFFFAOYSA-N ethyl 2-ethyl-5-methylpyrazole-3-carboxylate Chemical compound CCOC(=O)C1=CC(C)=NN1CC NTZFLNAMFHICLK-UHFFFAOYSA-N 0.000 description 1
- MVJRWZJSSDYLBG-UHFFFAOYSA-N ethyl 2-ethyl-5-propylpyrazole-3-carboxylate Chemical compound CCCC=1C=C(C(=O)OCC)N(CC)N=1 MVJRWZJSSDYLBG-UHFFFAOYSA-N 0.000 description 1
- PCWFEIRYFVRNSR-UHFFFAOYSA-N ethyl 3,5-dioxoheptanoate Chemical compound CCOC(=O)CC(=O)CC(=O)CC PCWFEIRYFVRNSR-UHFFFAOYSA-N 0.000 description 1
- HUOYGYKQFNULGK-UHFFFAOYSA-N ethyl 3,5-dioxononanoate Chemical compound CCCCC(=O)CC(=O)CC(=O)OCC HUOYGYKQFNULGK-UHFFFAOYSA-N 0.000 description 1
- GLPRPMUSFCMFIB-UHFFFAOYSA-N ethyl 3,5-dioxooctanoate;sodium Chemical compound [Na].CCCC(=O)CC(=O)CC(=O)OCC GLPRPMUSFCMFIB-UHFFFAOYSA-N 0.000 description 1
- HUQWMUKHIQSGDR-UHFFFAOYSA-N ethyl 4-ethyl-3,5-dioxohexanoate Chemical compound CCOC(=O)CC(=O)C(CC)C(C)=O HUQWMUKHIQSGDR-UHFFFAOYSA-N 0.000 description 1
- BOTXQJAHRCGJEG-UHFFFAOYSA-N ethyl 5-methyl-1h-pyrazole-3-carboxylate Chemical compound CCOC(=O)C=1C=C(C)NN=1 BOTXQJAHRCGJEG-UHFFFAOYSA-N 0.000 description 1
- 230000006203 ethylation Effects 0.000 description 1
- 238000006200 ethylation reaction Methods 0.000 description 1
- 239000002360 explosive Substances 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000000749 insecticidal effect Effects 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 238000009533 lab test Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- JUXFSTMNPMSURH-UHFFFAOYSA-N methyl 4,5-dimethyl-1h-pyrazole-3-carboxylate Chemical class COC(=O)C=1NN=C(C)C=1C JUXFSTMNPMSURH-UHFFFAOYSA-N 0.000 description 1
- 230000011987 methylation Effects 0.000 description 1
- 238000007069 methylation reaction Methods 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- YVZACCLFRNQBNO-UHFFFAOYSA-N pentylhydrazine Chemical compound CCCCCNN YVZACCLFRNQBNO-UHFFFAOYSA-N 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- JTJMJGYZQZDUJJ-UHFFFAOYSA-N phencyclidine Chemical compound C1CCCCN1C1(C=2C=CC=CC=2)CCCCC1 JTJMJGYZQZDUJJ-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229920000447 polyanionic polymer Polymers 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 150000003217 pyrazoles Chemical class 0.000 description 1
- 239000002760 rocket fuel Substances 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 230000002048 spasmolytic effect Effects 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000002227 vasoactive effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
- C07C69/67—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of saturated acids
- C07C69/716—Esters of keto-carboxylic acids or aldehydo-carboxylic acids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19829616.9 | 1998-07-02 | ||
| DE19829616A DE19829616A1 (de) | 1998-07-02 | 1998-07-02 | Verfahren zur Herstellung von 1-Alkyl-pyrazol-5-carbonsäureestern |
| PCT/EP1999/004297 WO2000001673A2 (de) | 1998-07-02 | 1999-06-21 | Verfahren zur herstellung von 1-alkyl-pyrazol-5-carbonsäureestern |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2336310A1 true CA2336310A1 (en) | 2000-01-13 |
Family
ID=7872783
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002336310A Abandoned CA2336310A1 (en) | 1998-07-02 | 1999-06-21 | Method for preparing 1-alkyl-pyrazol-5-carboxylic acid esters |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US6297386B1 (enExample) |
| EP (1) | EP1091940B1 (enExample) |
| JP (1) | JP2003513004A (enExample) |
| KR (1) | KR20010053253A (enExample) |
| CN (1) | CN1119335C (enExample) |
| AT (1) | ATE249441T1 (enExample) |
| CA (1) | CA2336310A1 (enExample) |
| DE (2) | DE19829616A1 (enExample) |
| ES (1) | ES2207952T3 (enExample) |
| HU (1) | HUP0204259A2 (enExample) |
| IL (1) | IL140156A0 (enExample) |
| PL (1) | PL364939A1 (enExample) |
| WO (1) | WO2000001673A2 (enExample) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0016787D0 (en) | 2000-07-07 | 2000-08-30 | Pfizer Ltd | Compounds useful in therapy |
| WO2009116435A1 (ja) * | 2008-03-18 | 2009-09-24 | 三井化学アグロ株式会社 | 含フッ素アシル酢酸誘導体の製造方法、含フッ素ピラゾールカルボン酸エステル誘導体の製造方法及び含フッ素ピラゾールカルボン酸誘導体の製造方法 |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3557095A (en) | 1968-05-31 | 1971-01-19 | Parke Davis & Co | Pyrazolodiazepinone compounds |
| DE2945657A1 (de) * | 1979-11-12 | 1981-05-21 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von pivaloylbrenztraubensaeureestern |
| JPS57106665A (en) * | 1980-12-23 | 1982-07-02 | Showa Denko Kk | 3-pyrazolecarboxamide derivative, its preparation, and herbicide |
| JPS6140266A (ja) * | 1984-08-01 | 1986-02-26 | Morishita Seiyaku Kk | ピラゾ−ル誘導体 |
| JP2861103B2 (ja) * | 1988-10-26 | 1999-02-24 | 日産化学工業株式会社 | ４―メチルピラゾール類の製造方法 |
| JP2743461B2 (ja) | 1989-05-08 | 1998-04-22 | 三菱化学株式会社 | １―メチル―３―アルキル―５―ピラゾールカルボン酸エステル類の製造法 |
| GB9013750D0 (en) | 1990-06-20 | 1990-08-08 | Pfizer Ltd | Therapeutic agents |
| JP3006091B2 (ja) * | 1990-12-25 | 2000-02-07 | 日本ヒドラジン工業株式会社 | 置換ピラゾールの製造方法 |
| GB9114760D0 (en) | 1991-07-09 | 1991-08-28 | Pfizer Ltd | Therapeutic agents |
| JP3491344B2 (ja) * | 1993-08-31 | 2004-01-26 | 宇部興産株式会社 | １−アルキル−５−ピラゾールカルボン酸エステル類の製法 |
| DE19701277A1 (de) * | 1997-01-16 | 1998-07-23 | Bayer Ag | Verfahren zur Herstellung von 1-Alkyl-pyrazol-5-carbonsäureestern |
-
1998
- 1998-07-02 DE DE19829616A patent/DE19829616A1/de not_active Withdrawn
-
1999
- 1999-06-21 IL IL14015699A patent/IL140156A0/xx unknown
- 1999-06-21 KR KR1020007014934A patent/KR20010053253A/ko not_active Withdrawn
- 1999-06-21 AT AT99931126T patent/ATE249441T1/de not_active IP Right Cessation
- 1999-06-21 HU HU0204259A patent/HUP0204259A2/hu unknown
- 1999-06-21 PL PL99364939A patent/PL364939A1/xx not_active Application Discontinuation
- 1999-06-21 US US09/720,010 patent/US6297386B1/en not_active Expired - Lifetime
- 1999-06-21 CA CA002336310A patent/CA2336310A1/en not_active Abandoned
- 1999-06-21 WO PCT/EP1999/004297 patent/WO2000001673A2/de not_active Ceased
- 1999-06-21 JP JP2000558078A patent/JP2003513004A/ja active Pending
- 1999-06-21 CN CN99808216A patent/CN1119335C/zh not_active Expired - Fee Related
- 1999-06-21 EP EP99931126A patent/EP1091940B1/de not_active Expired - Lifetime
- 1999-06-21 DE DE59906968T patent/DE59906968D1/de not_active Expired - Lifetime
- 1999-06-21 ES ES99931126T patent/ES2207952T3/es not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| KR20010053253A (ko) | 2001-06-25 |
| PL364939A1 (en) | 2004-12-27 |
| WO2000001673A2 (de) | 2000-01-13 |
| US6297386B1 (en) | 2001-10-02 |
| WO2000001673A3 (de) | 2002-09-26 |
| DE19829616A1 (de) | 2000-01-05 |
| ATE249441T1 (de) | 2003-09-15 |
| JP2003513004A (ja) | 2003-04-08 |
| CN1119335C (zh) | 2003-08-27 |
| ES2207952T3 (es) | 2004-06-01 |
| EP1091940B1 (de) | 2003-09-10 |
| HUP0204259A2 (hu) | 2003-03-28 |
| EP1091940A1 (de) | 2001-04-18 |
| DE59906968D1 (de) | 2003-10-16 |
| IL140156A0 (en) | 2002-02-10 |
| CN1308612A (zh) | 2001-08-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |