NO801496L - Fremgangsmaate ved fremstilling av pyrazolderivater - Google Patents
Fremgangsmaate ved fremstilling av pyrazolderivaterInfo
- Publication number
- NO801496L NO801496L NO801496A NO801496A NO801496L NO 801496 L NO801496 L NO 801496L NO 801496 A NO801496 A NO 801496A NO 801496 A NO801496 A NO 801496A NO 801496 L NO801496 L NO 801496L
- Authority
- NO
- Norway
- Prior art keywords
- pyrazole
- chlorophenyl
- fluorophenyl
- acetic acid
- solution
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 6
- -1 nitro, amino Chemical group 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims description 2
- 150000003217 pyrazoles Chemical class 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 239000011593 sulfur Substances 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims 3
- 229910052739 hydrogen Inorganic materials 0.000 claims 3
- 239000001257 hydrogen Substances 0.000 claims 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 2
- 150000007513 acids Chemical class 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 1
- 125000004414 alkyl thio group Chemical group 0.000 claims 1
- FJKIXWOMBXYWOQ-UHFFFAOYSA-N ethenoxyethane Chemical group CCOC=C FJKIXWOMBXYWOQ-UHFFFAOYSA-N 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 30
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000005457 ice water Substances 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 235000019341 magnesium sulphate Nutrition 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- UGAGMGHVRQLXKG-UHFFFAOYSA-N 1-(4-chlorophenyl)-n,n-dimethylethenamine Chemical compound CN(C)C(=C)C1=CC=C(Cl)C=C1 UGAGMGHVRQLXKG-UHFFFAOYSA-N 0.000 description 2
- BMMBSROJAOISIS-UHFFFAOYSA-N 1-[4-(4-chlorophenyl)-1-(4-fluorophenyl)pyrazol-3-yl]ethanone Chemical compound CC(=O)C1=NN(C=2C=CC(F)=CC=2)C=C1C1=CC=C(Cl)C=C1 BMMBSROJAOISIS-UHFFFAOYSA-N 0.000 description 2
- AZUYLZMQTIKGSC-UHFFFAOYSA-N 1-[6-[4-(5-chloro-6-methyl-1H-indazol-4-yl)-5-methyl-3-(1-methylindazol-5-yl)pyrazol-1-yl]-2-azaspiro[3.3]heptan-2-yl]prop-2-en-1-one Chemical compound ClC=1C(=C2C=NNC2=CC=1C)C=1C(=NN(C=1C)C1CC2(CN(C2)C(C=C)=O)C1)C=1C=C2C=NN(C2=CC=1)C AZUYLZMQTIKGSC-UHFFFAOYSA-N 0.000 description 2
- DHEUKGACTBHYCW-UHFFFAOYSA-N 2-[4-(4-chlorophenyl)-1-(4-methylsulfanylphenyl)pyrazol-3-yl]acetic acid Chemical compound ClC1=CC=C(C=C1)C=1C(=NN(C1)C1=CC=C(C=C1)SC)CC(=O)O DHEUKGACTBHYCW-UHFFFAOYSA-N 0.000 description 2
- RMCCCVIYWRJQEW-UHFFFAOYSA-N 4-[2-(4-bromophenyl)ethenyl]morpholine Chemical compound C1=CC(Br)=CC=C1C=CN1CCOCC1 RMCCCVIYWRJQEW-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 229950005499 carbon tetrachloride Drugs 0.000 description 2
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 2
- OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 description 2
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- GLYDHOZNBVJYBG-UHFFFAOYSA-N n-(4-fluorophenyl)-2-oxopropanehydrazonoyl chloride Chemical compound CC(=O)C(Cl)=NNC1=CC=C(F)C=C1 GLYDHOZNBVJYBG-UHFFFAOYSA-N 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- BHTZCIGVYSJBQB-UHFFFAOYSA-N 1-(1h-pyrazol-5-yl)ethanone Chemical class CC(=O)C=1C=CNN=1 BHTZCIGVYSJBQB-UHFFFAOYSA-N 0.000 description 1
- SDHFIWNBYPDKTQ-UHFFFAOYSA-N 1-[1,4-bis(4-chlorophenyl)pyrazol-3-yl]ethanone Chemical compound CC(=O)C1=NN(C=2C=CC(Cl)=CC=2)C=C1C1=CC=C(Cl)C=C1 SDHFIWNBYPDKTQ-UHFFFAOYSA-N 0.000 description 1
- YKJUQRWZPARTLM-UHFFFAOYSA-N 1-[4-(4-bromophenyl)-1-(4-fluorophenyl)pyrazol-3-yl]ethanone Chemical compound CC(=O)C1=NN(C=2C=CC(F)=CC=2)C=C1C1=CC=C(Br)C=C1 YKJUQRWZPARTLM-UHFFFAOYSA-N 0.000 description 1
- VMLSODMFKSZXDR-UHFFFAOYSA-N 1-[4-(4-bromophenyl)-2-(4-fluorophenyl)-3-morpholin-4-yl-3,4-dihydropyrazol-5-yl]ethanone Chemical compound CC(=O)C1=NN(C=2C=CC(F)=CC=2)C(N2CCOCC2)C1C1=CC=C(Br)C=C1 VMLSODMFKSZXDR-UHFFFAOYSA-N 0.000 description 1
- ZVPZZMHGAOROCC-UHFFFAOYSA-N 1-[4-(4-chlorophenyl)-1-(4-methylsulfanylphenyl)pyrazol-3-yl]ethanone Chemical compound C1=CC(SC)=CC=C1N1N=C(C(C)=O)C(C=2C=CC(Cl)=CC=2)=C1 ZVPZZMHGAOROCC-UHFFFAOYSA-N 0.000 description 1
- IRGRRSWKJQLVRB-UHFFFAOYSA-N 1-[4-(4-chlorophenyl)-1-phenylpyrazol-3-yl]ethanone Chemical compound CC(=O)C1=NN(C=2C=CC=CC=2)C=C1C1=CC=C(Cl)C=C1 IRGRRSWKJQLVRB-UHFFFAOYSA-N 0.000 description 1
- PQHKAMGAAKGSNW-UHFFFAOYSA-N 1-[4-(4-chlorophenyl)-2-(4-fluorophenyl)-3-morpholin-4-yl-3,4-dihydropyrazol-5-yl]ethanone Chemical compound CC(=O)C1=NN(C=2C=CC(F)=CC=2)C(N2CCOCC2)C1C1=CC=C(Cl)C=C1 PQHKAMGAAKGSNW-UHFFFAOYSA-N 0.000 description 1
- JQZAEUFPPSRDOP-UHFFFAOYSA-N 1-chloro-4-(chloromethyl)benzene Chemical compound ClCC1=CC=C(Cl)C=C1 JQZAEUFPPSRDOP-UHFFFAOYSA-N 0.000 description 1
- WPOYBLWKLDBTBP-UHFFFAOYSA-N 1-morpholin-4-ylethanethione Chemical class CC(=S)N1CCOCC1 WPOYBLWKLDBTBP-UHFFFAOYSA-N 0.000 description 1
- KEQTWHPMSVAFDA-UHFFFAOYSA-N 2,3-dihydro-1h-pyrazole Chemical compound C1NNC=C1 KEQTWHPMSVAFDA-UHFFFAOYSA-N 0.000 description 1
- MFHFWRBXPQDZSA-UHFFFAOYSA-N 2-(4-bromophenyl)acetonitrile Chemical compound BrC1=CC=C(CC#N)C=C1 MFHFWRBXPQDZSA-UHFFFAOYSA-N 0.000 description 1
- MWSNYBOKRSGWAN-UHFFFAOYSA-N 2-(4-chlorophenyl)acetaldehyde Chemical compound ClC1=CC=C(CC=O)C=C1 MWSNYBOKRSGWAN-UHFFFAOYSA-N 0.000 description 1
- QDNFDLUXFADBPV-UHFFFAOYSA-N 2-[1,4-bis(4-chlorophenyl)pyrazol-3-yl]-1-morpholin-4-ylethanethione Chemical compound C1=CC(Cl)=CC=C1C1=CN(C=2C=CC(Cl)=CC=2)N=C1CC(=S)N1CCOCC1 QDNFDLUXFADBPV-UHFFFAOYSA-N 0.000 description 1
- HMQSECTWUFQSPK-UHFFFAOYSA-N 2-[1,4-bis(4-fluorophenyl)pyrazol-3-yl]acetic acid Chemical compound OC(=O)CC1=NN(C=2C=CC(F)=CC=2)C=C1C1=CC=C(F)C=C1 HMQSECTWUFQSPK-UHFFFAOYSA-N 0.000 description 1
- TYBKLPOBJCHOCY-UHFFFAOYSA-N 2-[4-(3,4-dichlorophenyl)-1-(4-fluorophenyl)pyrazol-3-yl]acetic acid Chemical compound OC(=O)CC1=NN(C=2C=CC(F)=CC=2)C=C1C1=CC=C(Cl)C(Cl)=C1 TYBKLPOBJCHOCY-UHFFFAOYSA-N 0.000 description 1
- CUNUHKDDCQBLDQ-UHFFFAOYSA-N 2-[4-(4-bromophenyl)-1-(4-fluorophenyl)pyrazol-3-yl]-1-morpholin-4-ylethanethione Chemical compound C1=CC(F)=CC=C1N1N=C(CC(=S)N2CCOCC2)C(C=2C=CC(Br)=CC=2)=C1 CUNUHKDDCQBLDQ-UHFFFAOYSA-N 0.000 description 1
- NFLKDJLSLPLAGV-UHFFFAOYSA-N 2-[4-(4-bromophenyl)-1-(4-fluorophenyl)pyrazol-3-yl]acetic acid Chemical compound OC(=O)CC1=NN(C=2C=CC(F)=CC=2)C=C1C1=CC=C(Br)C=C1 NFLKDJLSLPLAGV-UHFFFAOYSA-N 0.000 description 1
- CNSPGYKKZSPRQS-UHFFFAOYSA-N 2-[4-(4-chlorophenyl)-1-(4-fluorophenyl)pyrazol-3-yl]-1-morpholin-4-ylethanethione Chemical compound C1=CC(F)=CC=C1N1N=C(CC(=S)N2CCOCC2)C(C=2C=CC(Cl)=CC=2)=C1 CNSPGYKKZSPRQS-UHFFFAOYSA-N 0.000 description 1
- YAMFWQIVVMITPG-UHFFFAOYSA-N 2-[4-(4-chlorophenyl)-1-(4-fluorophenyl)pyrazol-3-yl]acetic acid Chemical compound OC(=O)CC1=NN(C=2C=CC(F)=CC=2)C=C1C1=CC=C(Cl)C=C1 YAMFWQIVVMITPG-UHFFFAOYSA-N 0.000 description 1
- JLBVDJWADOVLAN-UHFFFAOYSA-N 2-[4-(4-chlorophenyl)-1-(4-methylsulfanylphenyl)pyrazol-3-yl]-1-morpholin-4-ylethanethione Chemical compound C1=CC(SC)=CC=C1N1N=C(CC(=S)N2CCOCC2)C(C=2C=CC(Cl)=CC=2)=C1 JLBVDJWADOVLAN-UHFFFAOYSA-N 0.000 description 1
- SOKWKFYFQMCYLX-UHFFFAOYSA-N 2-[4-(4-chlorophenyl)-1-(4-methylsulfinylphenyl)pyrazol-3-yl]acetic acid Chemical compound ClC1=CC=C(C=C1)C=1C(=NN(C1)C1=CC=C(C=C1)S(=O)C)CC(=O)O SOKWKFYFQMCYLX-UHFFFAOYSA-N 0.000 description 1
- WMJZPMJTHUVWSW-UHFFFAOYSA-N 2-[4-(4-chlorophenyl)-1-phenylpyrazol-3-yl]acetic acid Chemical compound OC(=O)CC1=NN(C=2C=CC=CC=2)C=C1C1=CC=C(Cl)C=C1 WMJZPMJTHUVWSW-UHFFFAOYSA-N 0.000 description 1
- VLRGXXKFHVJQOL-UHFFFAOYSA-N 3-chloropentane-2,4-dione Chemical compound CC(=O)C(Cl)C(C)=O VLRGXXKFHVJQOL-UHFFFAOYSA-N 0.000 description 1
- YKFROQCFVXOUPW-UHFFFAOYSA-N 4-(methylthio) aniline Chemical compound CSC1=CC=C(N)C=C1 YKFROQCFVXOUPW-UHFFFAOYSA-N 0.000 description 1
- AOAJHBQTGNMXKH-UHFFFAOYSA-N 4-[2-(4-chlorophenyl)ethenyl]morpholine Chemical compound C1=CC(Cl)=CC=C1C=CN1CCOCC1 AOAJHBQTGNMXKH-UHFFFAOYSA-N 0.000 description 1
- QSNSCYSYFYORTR-UHFFFAOYSA-N 4-chloroaniline Chemical compound NC1=CC=C(Cl)C=C1 QSNSCYSYFYORTR-UHFFFAOYSA-N 0.000 description 1
- IVYMIRMKXZAHRV-UHFFFAOYSA-N 4-chlorophenylacetonitrile Chemical compound ClC1=CC=C(CC#N)C=C1 IVYMIRMKXZAHRV-UHFFFAOYSA-N 0.000 description 1
- KRZCOLNOCZKSDF-UHFFFAOYSA-N 4-fluoroaniline Chemical compound NC1=CC=C(F)C=C1 KRZCOLNOCZKSDF-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- HASGOCLZFTZSTN-UHFFFAOYSA-N cyclohexane;hexane Chemical compound CCCCCC.C1CCCCC1 HASGOCLZFTZSTN-UHFFFAOYSA-N 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 229940050176 methyl chloride Drugs 0.000 description 1
- RJHCGGWBOWGPJS-UHFFFAOYSA-N n-(4-chlorophenyl)-2-oxopropanehydrazonoyl chloride Chemical compound CC(=O)C(Cl)=NNC1=CC=C(Cl)C=C1 RJHCGGWBOWGPJS-UHFFFAOYSA-N 0.000 description 1
- HOCCFPYBPMPQRB-UHFFFAOYSA-N n-(4-methylsulfanylphenyl)-2-oxopropanehydrazonoyl chloride Chemical compound CSC1=CC=C(NN=C(Cl)C(C)=O)C=C1 HOCCFPYBPMPQRB-UHFFFAOYSA-N 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- IYJCSNRIDBJVRP-UHFFFAOYSA-M sodium;2-[4-(4-chlorophenyl)-1-(4-fluorophenyl)pyrazol-3-yl]acetate Chemical compound [Na+].[O-]C(=O)CC1=NN(C=2C=CC(F)=CC=2)C=C1C1=CC=C(Cl)C=C1 IYJCSNRIDBJVRP-UHFFFAOYSA-M 0.000 description 1
- DGPIGKCOQYBCJH-UHFFFAOYSA-M sodium;acetic acid;hydroxide Chemical compound O.[Na+].CC([O-])=O DGPIGKCOQYBCJH-UHFFFAOYSA-M 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 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
- C07D231/06—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
-
- 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
- C07D231/12—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 only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19792920941 DE2920941A1 (de) | 1979-05-21 | 1979-05-21 | Verfahren zur herstellung von pyrazol- derivaten |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO801496L true NO801496L (no) | 1980-11-24 |
Family
ID=6071550
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO801496A NO801496L (no) | 1979-05-21 | 1980-05-20 | Fremgangsmaate ved fremstilling av pyrazolderivater |
Country Status (6)
| Country | Link |
|---|---|
| DE (1) | DE2920941A1 (enExample) |
| DK (1) | DK151626C (enExample) |
| FI (1) | FI77655C (enExample) |
| GR (1) | GR68455B (enExample) |
| HU (1) | HU185383B (enExample) |
| NO (1) | NO801496L (enExample) |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE748539C (de) * | 1941-01-16 | 1944-11-06 | Verfahren zur Herstellung der Amide heterocyclich substituierter Essigsaeuren bzw. der freien Saeuren |
-
1979
- 1979-05-21 DE DE19792920941 patent/DE2920941A1/de not_active Withdrawn
-
1980
- 1980-05-19 GR GR61980A patent/GR68455B/el unknown
- 1980-05-20 NO NO801496A patent/NO801496L/no unknown
- 1980-05-20 DK DK219180A patent/DK151626C/da not_active IP Right Cessation
- 1980-05-20 HU HU801259A patent/HU185383B/hu unknown
- 1980-05-21 FI FI801639A patent/FI77655C/fi not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| FI801639A7 (fi) | 1980-11-22 |
| DE2920941A1 (de) | 1980-11-27 |
| DK151626C (da) | 1988-07-18 |
| FI77655C (fi) | 1989-04-10 |
| HU185383B (en) | 1985-01-28 |
| DK219180A (da) | 1980-11-22 |
| GR68455B (enExample) | 1981-12-30 |
| FI77655B (fi) | 1988-12-30 |
| DK151626B (da) | 1987-12-21 |
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