HU209868B - Process for production of phenyl -1,2,4-triazoline-5-one derivatives - Google Patents
Process for production of phenyl -1,2,4-triazoline-5-one derivatives Download PDFInfo
- Publication number
- HU209868B HU209868B HU9200771A HU77192A HU209868B HU 209868 B HU209868 B HU 209868B HU 9200771 A HU9200771 A HU 9200771A HU 77192 A HU77192 A HU 77192A HU 209868 B HU209868 B HU 209868B
- Authority
- HU
- Hungary
- Prior art keywords
- formula
- compound
- alkyl
- phenyl
- process according
- Prior art date
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- 238000000034 method Methods 0.000 title claims abstract description 30
- 230000008569 process Effects 0.000 title claims abstract description 29
- OEOLYHPXIMTFSD-UHFFFAOYSA-N 3-phenyl-3,4-dihydro-1,2,4-triazol-5-one Chemical class N1=NC(=O)NC1C1=CC=CC=C1 OEOLYHPXIMTFSD-UHFFFAOYSA-N 0.000 title claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 25
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 13
- 150000002367 halogens Chemical group 0.000 claims abstract description 13
- -1 aryl triazolinone Chemical compound 0.000 claims abstract description 11
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 11
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000000460 chlorine Substances 0.000 claims abstract description 10
- 239000002253 acid Substances 0.000 claims abstract description 8
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims abstract description 8
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 6
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims abstract description 5
- 125000004414 alkyl thio group Chemical group 0.000 claims abstract description 5
- 150000003839 salts Chemical class 0.000 claims abstract description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 4
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims abstract description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 4
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 4
- 125000004966 cyanoalkyl group Chemical group 0.000 claims abstract description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 3
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims abstract 2
- 238000006243 chemical reaction Methods 0.000 claims description 35
- 150000001875 compounds Chemical class 0.000 claims description 31
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims description 24
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 claims description 19
- 239000005708 Sodium hypochlorite Substances 0.000 claims description 13
- WQYVRQLZKVEZGA-UHFFFAOYSA-N hypochlorite Chemical compound Cl[O-] WQYVRQLZKVEZGA-UHFFFAOYSA-N 0.000 claims description 12
- DYFVFCJGOSGDKA-UHFFFAOYSA-N 1-phenyltriazolidin-4-one Chemical class N1NC(=O)CN1C1=CC=CC=C1 DYFVFCJGOSGDKA-UHFFFAOYSA-N 0.000 claims description 10
- 238000002360 preparation method Methods 0.000 claims description 8
- 229910052783 alkali metal Inorganic materials 0.000 claims description 6
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 5
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 238000002955 isolation Methods 0.000 claims description 4
- 239000007858 starting material Substances 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 238000011065 in-situ storage Methods 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 6
- 239000007788 liquid Substances 0.000 claims 3
- 239000000725 suspension Substances 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- KURBTRNHGDQKOS-XNWCZRBMSA-N n-[(e)-ethylideneamino]aniline Chemical compound C\C=N\NC1=CC=CC=C1 KURBTRNHGDQKOS-XNWCZRBMSA-N 0.000 claims 1
- XMVJITFPVVRMHC-UHFFFAOYSA-N roxarsone Chemical group OC1=CC=C([As](O)(O)=O)C=C1[N+]([O-])=O XMVJITFPVVRMHC-UHFFFAOYSA-N 0.000 claims 1
- 125000006350 alkyl thio alkyl group Chemical group 0.000 abstract description 3
- 229960005437 etoperidone Drugs 0.000 abstract description 3
- 125000004687 alkyl sulfinyl alkyl group Chemical group 0.000 abstract description 2
- 125000004688 alkyl sulfonyl alkyl group Chemical group 0.000 abstract description 2
- 125000003118 aryl group Chemical group 0.000 abstract description 2
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- 125000001188 haloalkyl group Chemical group 0.000 abstract 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 41
- 239000000243 solution Substances 0.000 description 24
- 239000000203 mixture Substances 0.000 description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
- 239000011541 reaction mixture Substances 0.000 description 20
- 239000007787 solid Substances 0.000 description 17
- 229960000583 acetic acid Drugs 0.000 description 16
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- 238000003756 stirring Methods 0.000 description 11
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 10
- 239000000706 filtrate Substances 0.000 description 10
- 150000007857 hydrazones Chemical class 0.000 description 10
- 239000002244 precipitate Substances 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- GKKCIDNWFBPDBW-UHFFFAOYSA-M potassium cyanate Chemical compound [K]OC#N GKKCIDNWFBPDBW-UHFFFAOYSA-M 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 238000001914 filtration Methods 0.000 description 6
- 239000012362 glacial acetic acid Substances 0.000 description 6
- 239000000543 intermediate Substances 0.000 description 6
- 238000006722 reduction reaction Methods 0.000 description 6
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 5
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 5
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 5
- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 description 5
- 230000009467 reduction Effects 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- 238000005481 NMR spectroscopy Methods 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 230000037361 pathway Effects 0.000 description 4
- HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 description 4
- 229940067157 phenylhydrazine Drugs 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
- SZUVGFMDDVSKSI-WIFOCOSTSA-N (1s,2s,3s,5r)-1-(carboxymethyl)-3,5-bis[(4-phenoxyphenyl)methyl-propylcarbamoyl]cyclopentane-1,2-dicarboxylic acid Chemical compound O=C([C@@H]1[C@@H]([C@](CC(O)=O)([C@H](C(=O)N(CCC)CC=2C=CC(OC=3C=CC=CC=3)=CC=2)C1)C(O)=O)C(O)=O)N(CCC)CC(C=C1)=CC=C1OC1=CC=CC=C1 SZUVGFMDDVSKSI-WIFOCOSTSA-N 0.000 description 3
- UNILWMWFPHPYOR-KXEYIPSPSA-M 1-[6-[2-[3-[3-[3-[2-[2-[3-[[2-[2-[[(2r)-1-[[2-[[(2r)-1-[3-[2-[2-[3-[[2-(2-amino-2-oxoethoxy)acetyl]amino]propoxy]ethoxy]ethoxy]propylamino]-3-hydroxy-1-oxopropan-2-yl]amino]-2-oxoethyl]amino]-3-[(2r)-2,3-di(hexadecanoyloxy)propyl]sulfanyl-1-oxopropan-2-yl Chemical compound O=C1C(SCCC(=O)NCCCOCCOCCOCCCNC(=O)COCC(=O)N[C@@H](CSC[C@@H](COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCC)C(=O)NCC(=O)N[C@H](CO)C(=O)NCCCOCCOCCOCCCNC(=O)COCC(N)=O)CC(=O)N1CCNC(=O)CCCCCN\1C2=CC=C(S([O-])(=O)=O)C=C2CC/1=C/C=C/C=C/C1=[N+](CC)C2=CC=C(S([O-])(=O)=O)C=C2C1 UNILWMWFPHPYOR-KXEYIPSPSA-M 0.000 description 3
- RDDFSTCCJVTFPR-UHFFFAOYSA-N 5-methyl-2-(3-nitrophenyl)-1,2,4-triazolidin-3-one Chemical compound O=C1NC(C)NN1C1=CC=CC([N+]([O-])=O)=C1 RDDFSTCCJVTFPR-UHFFFAOYSA-N 0.000 description 3
- KQHAMBITCFATGC-UHFFFAOYSA-N 5-methyl-2-(3-nitrophenyl)-1h-1,2,4-triazol-3-one Chemical compound O=C1NC(C)=NN1C1=CC=CC([N+]([O-])=O)=C1 KQHAMBITCFATGC-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 239000007844 bleaching agent Substances 0.000 description 3
- 229940126543 compound 14 Drugs 0.000 description 3
- IZBNNCFOBMGTQX-UHFFFAOYSA-N etoperidone Chemical class O=C1N(CC)C(CC)=NN1CCCN1CCN(C=2C=C(Cl)C=CC=2)CC1 IZBNNCFOBMGTQX-UHFFFAOYSA-N 0.000 description 3
- 239000012065 filter cake Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- ZVCDLGYNFYZZOK-UHFFFAOYSA-M sodium cyanate Chemical compound [Na]OC#N ZVCDLGYNFYZZOK-UHFFFAOYSA-M 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- UDQTXCHQKHIQMH-KYGLGHNPSA-N (3ar,5s,6s,7r,7ar)-5-(difluoromethyl)-2-(ethylamino)-5,6,7,7a-tetrahydro-3ah-pyrano[3,2-d][1,3]thiazole-6,7-diol Chemical compound S1C(NCC)=N[C@H]2[C@@H]1O[C@H](C(F)F)[C@@H](O)[C@@H]2O UDQTXCHQKHIQMH-KYGLGHNPSA-N 0.000 description 2
- OMBVEVHRIQULKW-DNQXCXABSA-M (3r,5r)-7-[3-(4-fluorophenyl)-8-oxo-7-phenyl-1-propan-2-yl-5,6-dihydro-4h-pyrrolo[2,3-c]azepin-2-yl]-3,5-dihydroxyheptanoate Chemical compound O=C1C=2N(C(C)C)C(CC[C@@H](O)C[C@@H](O)CC([O-])=O)=C(C=3C=CC(F)=CC=3)C=2CCCN1C1=CC=CC=C1 OMBVEVHRIQULKW-DNQXCXABSA-M 0.000 description 2
- ADXQSKYXLBIQSO-UHFFFAOYSA-N 2-(4-chloro-3-nitrophenyl)-5-methyl-1h-1,2,4-triazol-3-one Chemical compound O=C1NC(C)=NN1C1=CC=C(Cl)C([N+]([O-])=O)=C1 ADXQSKYXLBIQSO-UHFFFAOYSA-N 0.000 description 2
- QSNSCYSYFYORTR-UHFFFAOYSA-N 4-chloroaniline Chemical compound NC1=CC=C(Cl)C=C1 QSNSCYSYFYORTR-UHFFFAOYSA-N 0.000 description 2
- GZHGJANWGGNBRJ-UHFFFAOYSA-N 5-methyl-2-phenyl-1,2,4-triazolidin-3-one Chemical compound O=C1NC(C)NN1C1=CC=CC=C1 GZHGJANWGGNBRJ-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
- 229910021626 Tin(II) chloride Inorganic materials 0.000 description 2
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 150000001448 anilines Chemical class 0.000 description 2
- JFBJUMZWZDHTIF-UHFFFAOYSA-N chlorine chlorite Inorganic materials ClOCl=O JFBJUMZWZDHTIF-UHFFFAOYSA-N 0.000 description 2
- 229940126540 compound 41 Drugs 0.000 description 2
- 229940125936 compound 42 Drugs 0.000 description 2
- 238000006193 diazotization reaction Methods 0.000 description 2
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- JGJLWPGRMCADHB-UHFFFAOYSA-N hypobromite Chemical compound Br[O-] JGJLWPGRMCADHB-UHFFFAOYSA-N 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- OHRWLUAIBLJRNI-UHFFFAOYSA-N n-(5-amino-2-chlorophenyl)methanesulfonamide Chemical compound CS(=O)(=O)NC1=CC(N)=CC=C1Cl OHRWLUAIBLJRNI-UHFFFAOYSA-N 0.000 description 2
- 229910017604 nitric acid Inorganic materials 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000012429 reaction media Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000010288 sodium nitrite Nutrition 0.000 description 2
- 235000011150 stannous chloride Nutrition 0.000 description 2
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 2
- AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 2
- ZTPAUBJZUBGGEY-UHFFFAOYSA-N (2,4-dichlorophenyl)hydrazine Chemical compound NNC1=CC=C(Cl)C=C1Cl ZTPAUBJZUBGGEY-UHFFFAOYSA-N 0.000 description 1
- QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 1
- YQOLEILXOBUDMU-KRWDZBQOSA-N (4R)-5-[(6-bromo-3-methyl-2-pyrrolidin-1-ylquinoline-4-carbonyl)amino]-4-(2-chlorophenyl)pentanoic acid Chemical compound CC1=C(C2=C(C=CC(=C2)Br)N=C1N3CCCC3)C(=O)NC[C@H](CCC(=O)O)C4=CC=CC=C4Cl YQOLEILXOBUDMU-KRWDZBQOSA-N 0.000 description 1
- 125000004455 (C1-C3) alkylthio group Chemical group 0.000 description 1
- MUZVVLYZSISWDW-UHFFFAOYSA-N 1-phenyl-4h-triazol-5-one Chemical compound O=C1CN=NN1C1=CC=CC=C1 MUZVVLYZSISWDW-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- OGZJMGKRQOOSQE-UHFFFAOYSA-N 2-(2-chloro-5-nitrophenyl)-5-methyl-1h-1,2,4-triazol-3-one Chemical compound O=C1NC(C)=NN1C1=CC([N+]([O-])=O)=CC=C1Cl OGZJMGKRQOOSQE-UHFFFAOYSA-N 0.000 description 1
- CMCHJOMWXMRIDO-UHFFFAOYSA-N 2-(4-chlorophenyl)-5-methyl-1h-1,2,4-triazol-3-one Chemical compound O=C1NC(C)=NN1C1=CC=C(Cl)C=C1 CMCHJOMWXMRIDO-UHFFFAOYSA-N 0.000 description 1
- KWIXNFOTNVKIGM-UHFFFAOYSA-N 2-chloro-5-nitroaniline Chemical compound NC1=CC([N+]([O-])=O)=CC=C1Cl KWIXNFOTNVKIGM-UHFFFAOYSA-N 0.000 description 1
- AKCRQHGQIJBRMN-UHFFFAOYSA-N 2-chloroaniline Chemical compound NC1=CC=CC=C1Cl AKCRQHGQIJBRMN-UHFFFAOYSA-N 0.000 description 1
- AUSRSVRJOXYXMI-UHFFFAOYSA-N 2-methylsulfonylaniline Chemical compound CS(=O)(=O)C1=CC=CC=C1N AUSRSVRJOXYXMI-UHFFFAOYSA-N 0.000 description 1
- XJCVRTZCHMZPBD-UHFFFAOYSA-N 3-nitroaniline Chemical compound NC1=CC=CC([N+]([O-])=O)=C1 XJCVRTZCHMZPBD-UHFFFAOYSA-N 0.000 description 1
- FOHHWGVAOVDVLP-UHFFFAOYSA-N 4-chloro-3-nitroaniline Chemical compound NC1=CC=C(Cl)C([N+]([O-])=O)=C1 FOHHWGVAOVDVLP-UHFFFAOYSA-N 0.000 description 1
- IUQWBBIRBDXGFL-UHFFFAOYSA-N 4-chloro-n-(ethylideneamino)-3-nitroaniline Chemical compound CC=NNC1=CC=C(Cl)C([N+]([O-])=O)=C1 IUQWBBIRBDXGFL-UHFFFAOYSA-N 0.000 description 1
- KCBAMQOKOLXLOX-BSZYMOERSA-N CC1=C(SC=N1)C2=CC=C(C=C2)[C@H](C)NC(=O)[C@@H]3C[C@H](CN3C(=O)[C@H](C(C)(C)C)NC(=O)CCCCCCCCCCNCCCONC(=O)C4=C(C(=C(C=C4)F)F)NC5=C(C=C(C=C5)I)F)O Chemical compound CC1=C(SC=N1)C2=CC=C(C=C2)[C@H](C)NC(=O)[C@@H]3C[C@H](CN3C(=O)[C@H](C(C)(C)C)NC(=O)CCCCCCCCCCNCCCONC(=O)C4=C(C(=C(C=C4)F)F)NC5=C(C=C(C=C5)I)F)O KCBAMQOKOLXLOX-BSZYMOERSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
- SPXSEZMVRJLHQG-XMMPIXPASA-N [(2R)-1-[[4-[(3-phenylmethoxyphenoxy)methyl]phenyl]methyl]pyrrolidin-2-yl]methanol Chemical compound C(C1=CC=CC=C1)OC=1C=C(OCC2=CC=C(CN3[C@H](CCC3)CO)C=C2)C=CC=1 SPXSEZMVRJLHQG-XMMPIXPASA-N 0.000 description 1
- SFYLHIMXJQGKGZ-RQOWECAXSA-N acetaldehyde (Z)-hydrazone Chemical compound C\C=N/N SFYLHIMXJQGKGZ-RQOWECAXSA-N 0.000 description 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000003570 air Substances 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- XRWSZZJLZRKHHD-WVWIJVSJSA-N asunaprevir Chemical compound O=C([C@@H]1C[C@H](CN1C(=O)[C@@H](NC(=O)OC(C)(C)C)C(C)(C)C)OC1=NC=C(C2=CC=C(Cl)C=C21)OC)N[C@]1(C(=O)NS(=O)(=O)C2CC2)C[C@H]1C=C XRWSZZJLZRKHHD-WVWIJVSJSA-N 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 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
- 239000006227 byproduct Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- KYKAJFCTULSVSH-UHFFFAOYSA-N chloro(fluoro)methane Chemical compound F[C]Cl KYKAJFCTULSVSH-UHFFFAOYSA-N 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- 229940125833 compound 23 Drugs 0.000 description 1
- 229940125961 compound 24 Drugs 0.000 description 1
- 229940125844 compound 46 Drugs 0.000 description 1
- 229940127271 compound 49 Drugs 0.000 description 1
- 150000008049 diazo compounds Chemical class 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 150000002429 hydrazines Chemical class 0.000 description 1
- QWPPOHNGKGFGJK-UHFFFAOYSA-N hypochlorous acid Chemical compound ClO QWPPOHNGKGFGJK-UHFFFAOYSA-N 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- LWXVCCOAQYNXNX-UHFFFAOYSA-N lithium hypochlorite Chemical compound [Li+].Cl[O-] LWXVCCOAQYNXNX-UHFFFAOYSA-N 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- 125000004092 methylthiomethyl group Chemical group [H]C([H])([H])SC([H])([H])* 0.000 description 1
- HFRRHHSEMHKKIK-UHFFFAOYSA-N n-(2-chloro-5-nitrophenyl)methanesulfonamide Chemical compound CS(=O)(=O)NC1=CC([N+]([O-])=O)=CC=C1Cl HFRRHHSEMHKKIK-UHFFFAOYSA-N 0.000 description 1
- TWNIVRGCQWMALE-UHFFFAOYSA-N n-(ethylideneamino)-3-nitroaniline Chemical compound CC=NNC1=CC=CC([N+]([O-])=O)=C1 TWNIVRGCQWMALE-UHFFFAOYSA-N 0.000 description 1
- VWONRLCRTWBFHH-UHFFFAOYSA-N n-[2,4-dichloro-5-(5-methyl-3-oxo-1h-1,2,4-triazol-2-yl)phenyl]methanesulfonamide Chemical compound N1C(C)=NC(=O)N1C1=CC(NS(C)(=O)=O)=C(Cl)C=C1Cl VWONRLCRTWBFHH-UHFFFAOYSA-N 0.000 description 1
- WRZKZIGDSAEDKD-UHFFFAOYSA-N n-[2-chloro-5-(3-methyl-5-oxo-1,2,4-triazolidin-1-yl)phenyl]methanesulfonamide Chemical compound O=C1NC(C)NN1C1=CC=C(Cl)C(NS(C)(=O)=O)=C1 WRZKZIGDSAEDKD-UHFFFAOYSA-N 0.000 description 1
- OWXTXAWXSPNZFE-UHFFFAOYSA-N n-[2-chloro-5-(5-methyl-3-oxo-1h-1,2,4-triazol-2-yl)phenyl]methanesulfonamide Chemical compound O=C1NC(C)=NN1C1=CC=C(Cl)C(NS(C)(=O)=O)=C1 OWXTXAWXSPNZFE-UHFFFAOYSA-N 0.000 description 1
- IOMMMLWIABWRKL-WUTDNEBXSA-N nazartinib Chemical compound C1N(C(=O)/C=C/CN(C)C)CCCC[C@H]1N1C2=C(Cl)C=CC=C2N=C1NC(=O)C1=CC=NC(C)=C1 IOMMMLWIABWRKL-WUTDNEBXSA-N 0.000 description 1
- 238000006396 nitration reaction Methods 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000003444 phase transfer catalyst Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- HIFJUMGIHIZEPX-UHFFFAOYSA-N sulfuric acid;sulfur trioxide Chemical compound O=S(=O)=O.OS(O)(=O)=O HIFJUMGIHIZEPX-UHFFFAOYSA-N 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- GZNAASVAJNXPPW-UHFFFAOYSA-M tin(4+) chloride dihydrate Chemical compound O.O.[Cl-].[Sn+4] GZNAASVAJNXPPW-UHFFFAOYSA-M 0.000 description 1
- FWPIDFUJEMBDLS-UHFFFAOYSA-L tin(II) chloride dihydrate Substances O.O.Cl[Sn]Cl FWPIDFUJEMBDLS-UHFFFAOYSA-L 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles 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
- C07D249/12—Oxygen or sulfur atoms
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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US07/405,179 US4980480A (en) | 1989-09-08 | 1989-09-08 | Production of triazolinones |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| HU9200771D0 HU9200771D0 (en) | 1992-05-28 |
| HUT60725A HUT60725A (en) | 1992-10-28 |
| HU209868B true HU209868B (en) | 1994-11-28 |
Family
ID=23602610
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU9200771A HU209868B (en) | 1989-09-08 | 1990-08-21 | Process for production of phenyl -1,2,4-triazoline-5-one derivatives |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US4980480A (enExample) |
| EP (1) | EP0490936B1 (enExample) |
| JP (1) | JPH0678322B2 (enExample) |
| KR (1) | KR940009526B1 (enExample) |
| BR (1) | BR9007634A (enExample) |
| CA (1) | CA2059531C (enExample) |
| DE (1) | DE69028990T2 (enExample) |
| DK (1) | DK0490936T3 (enExample) |
| HU (1) | HU209868B (enExample) |
| IL (1) | IL95559A (enExample) |
| MX (1) | MX172079B (enExample) |
| RU (1) | RU2060994C1 (enExample) |
| TR (1) | TR24939A (enExample) |
| WO (1) | WO1991003470A1 (enExample) |
| ZA (1) | ZA906631B (enExample) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4238125A1 (de) * | 1992-11-12 | 1994-05-19 | Bayer Ag | Substituierte Triazolinone |
| US6906006B1 (en) | 1988-11-23 | 2005-06-14 | Bayer Aktiengesellschaft | N-arly-substituted nitrogen-containing heterocycles, processes and novel intermediates for their preparation, and their use as herbicides and plant growth regulators |
| US5440045A (en) * | 1992-05-13 | 1995-08-08 | Fmc Corporation | Triazolinone ring formation in tert-butanol |
| US5256793A (en) * | 1992-05-13 | 1993-10-26 | Fmc Corporation | Triazolinone ring formation in tert-butanol |
| US5468868A (en) * | 1993-12-16 | 1995-11-21 | Fmc Corporation | Process for the selective chlorination of 4,5-dihydro-1-phenyl-1H-1,2,4-triazol-5-one |
| US5449784A (en) * | 1994-06-22 | 1995-09-12 | Fmc Corporation | Method of preparing aryl triazolinones with trialkyl orthoacetates |
| JP3824648B2 (ja) * | 1995-08-21 | 2006-09-20 | エフ エム シー コーポレーション | 殺草性エチルα−２−ジクロロ−５−〔４−（ジフルオロメチル）−４，５−ジヒドロ−３−メチル−５−オキソ−１Ｈ−１，２，４−トリアゾール−１−イル〕−４−フルオロベンゼンプロパノエートの製造方法 |
| AR020273A1 (es) | 1998-08-27 | 2002-05-02 | Fmc Corp | Fluoracion regioselectiva de triazolinonas fenilo-sustituidas |
| US6492527B1 (en) | 1999-10-13 | 2002-12-10 | Fmc Corporation | Process to prepare aryltriazolinones and novel intermediates thereto |
| DE10031825A1 (de) * | 2000-06-30 | 2002-01-10 | Bayer Ag | Selektive Herbizide auf Basis von Arylsulfonylaminocarbonyltriazolinonen |
| JP3863736B2 (ja) * | 2000-08-08 | 2006-12-27 | 北興化学工業株式会社 | アリールトリアゾリノン類の製造法 |
| CN101910139B (zh) * | 2008-01-10 | 2012-09-26 | 北兴化学工业株式会社 | 苯基三唑啉酮类的制造方法 |
| US8669371B2 (en) | 2011-09-21 | 2014-03-11 | Bomi Patel Framroze | Regioselective chlorination of the phenyl ring of 4,5-dihydro-1-phenyl-1H-1,2,4-triazol-5-ones |
| CN103951627B (zh) * | 2014-05-06 | 2017-04-19 | 泸州东方农化有限公司 | 一种合成甲磺草胺中间体和甲磺草胺的方法 |
| CN104672157B (zh) * | 2015-02-12 | 2017-06-27 | 山东潍坊润丰化工股份有限公司 | 一种芳基三唑啉酮的制备方法 |
| CN112225705B (zh) * | 2020-11-20 | 2022-06-07 | 湖南海利常德农药化工有限公司 | 一种3-甲基-1-苯基-1h-1,2,4-三唑-5(4h)-酮的制备方法 |
| CN116120248A (zh) * | 2023-02-02 | 2023-05-16 | 宁夏格瑞精细化工有限公司 | 一种芳基三唑啉酮的制备方法 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1096333B (it) * | 1978-05-25 | 1985-08-26 | Montedison Spa | 1,2,4-triazolidin-3-oni e-tioni |
| DE3244657A1 (de) * | 1982-12-02 | 1984-06-07 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von triazolin-3,5-dionen |
| JPS60136573A (ja) * | 1983-12-26 | 1985-07-20 | Nippon Nohyaku Co Ltd | １，２，４−トリアゾロン誘導体の製造方法 |
| JPS60136572A (ja) * | 1983-12-26 | 1985-07-20 | Nippon Nohyaku Co Ltd | トリアゾロン誘導体の製造方法 |
| CN85106905A (zh) * | 1985-08-08 | 1987-02-04 | Fmc公司 | 含有1-芳基-δ2-1，2，4，-三唑啉-5-酮类的除草剂及其制备方法 |
| JPS6393768A (ja) * | 1986-10-08 | 1988-04-25 | Nippon Nohyaku Co Ltd | １，２，４−トリアゾリン−５−オン誘導体の製造方法 |
-
1989
- 1989-09-08 US US07/405,179 patent/US4980480A/en not_active Expired - Lifetime
-
1990
- 1990-08-21 DK DK90913149.2T patent/DK0490936T3/da active
- 1990-08-21 CA CA002059531A patent/CA2059531C/en not_active Expired - Fee Related
- 1990-08-21 EP EP90913149A patent/EP0490936B1/en not_active Expired - Lifetime
- 1990-08-21 BR BR909007634A patent/BR9007634A/pt not_active IP Right Cessation
- 1990-08-21 WO PCT/US1990/004742 patent/WO1991003470A1/en not_active Ceased
- 1990-08-21 DE DE69028990T patent/DE69028990T2/de not_active Expired - Fee Related
- 1990-08-21 ZA ZA906631A patent/ZA906631B/xx unknown
- 1990-08-21 RU SU905011519A patent/RU2060994C1/ru not_active IP Right Cessation
- 1990-08-21 JP JP2-512282A patent/JPH0678322B2/ja not_active Expired - Lifetime
- 1990-08-21 KR KR1019920700520A patent/KR940009526B1/ko not_active Expired - Fee Related
- 1990-08-21 HU HU9200771A patent/HU209868B/hu unknown
- 1990-08-31 IL IL9555990A patent/IL95559A/en not_active IP Right Cessation
- 1990-09-07 MX MX022293A patent/MX172079B/es unknown
- 1990-09-19 TR TR90/0809A patent/TR24939A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DE69028990T2 (de) | 1997-03-20 |
| DK0490936T3 (da) | 1996-11-18 |
| EP0490936A1 (en) | 1992-06-24 |
| EP0490936A4 (en) | 1992-10-14 |
| RU2060994C1 (ru) | 1996-05-27 |
| TR24939A (tr) | 1992-07-01 |
| CA2059531C (en) | 1993-10-05 |
| DE69028990D1 (de) | 1996-11-28 |
| HUT60725A (en) | 1992-10-28 |
| US4980480A (en) | 1990-12-25 |
| MX172079B (es) | 1993-12-01 |
| WO1991003470A1 (en) | 1991-03-21 |
| BR9007634A (pt) | 1992-07-07 |
| JPH0678322B2 (ja) | 1994-10-05 |
| IL95559A0 (en) | 1991-06-30 |
| JPH0678322B1 (enExample) | 1994-10-05 |
| IL95559A (en) | 1994-07-31 |
| KR927003548A (ko) | 1992-12-18 |
| EP0490936B1 (en) | 1996-10-23 |
| ZA906631B (en) | 1991-06-26 |
| CA2059531A1 (en) | 1991-03-09 |
| KR940009526B1 (ko) | 1994-10-14 |
| HU9200771D0 (en) | 1992-05-28 |
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