TW201711566A - 製備ｎ－（１，３，４－㗁二唑－２－基）芳基甲醯胺之方法 - Google Patents
製備ｎ－（１，３，４－㗁二唑－２－基）芳基甲醯胺之方法 Download PDFInfo
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- TW201711566A TW201711566A TW105129443A TW105129443A TW201711566A TW 201711566 A TW201711566 A TW 201711566A TW 105129443 A TW105129443 A TW 105129443A TW 105129443 A TW105129443 A TW 105129443A TW 201711566 A TW201711566 A TW 201711566A
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- Prior art keywords
- methyl
- formula
- alkyl
- iii
- chloride
- Prior art date
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- 238000000034 method Methods 0.000 title claims abstract description 30
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 9
- 239000001257 hydrogen Substances 0.000 claims abstract description 9
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 9
- 125000001424 substituent group Chemical group 0.000 claims abstract description 3
- ITQTTZVARXURQS-UHFFFAOYSA-N 3-methylpyridine Chemical compound CC1=CC=CN=C1 ITQTTZVARXURQS-UHFFFAOYSA-N 0.000 claims description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
- 150000001875 compounds Chemical class 0.000 claims description 12
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 9
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 8
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 7
- 239000012190 activator Substances 0.000 claims description 7
- 239000002904 solvent Substances 0.000 claims description 7
- NTSLROIKFLNUIJ-UHFFFAOYSA-N 5-Ethyl-2-methylpyridine Chemical compound CCC1=CC=C(C)N=C1 NTSLROIKFLNUIJ-UHFFFAOYSA-N 0.000 claims description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 6
- 239000003153 chemical reaction reagent Substances 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 239000005711 Benzoic acid Substances 0.000 claims description 5
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 5
- 235000010233 benzoic acid Nutrition 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- -1 methylthio, methyl Chemical group 0.000 claims description 5
- 125000004287 oxazol-2-yl group Chemical group [H]C1=C([H])N=C(*)O1 0.000 claims description 5
- 230000003213 activating effect Effects 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
- HCUYBXPSSCRKRF-UHFFFAOYSA-N diphosgene Chemical compound ClC(=O)OC(Cl)(Cl)Cl HCUYBXPSSCRKRF-UHFFFAOYSA-N 0.000 claims description 4
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 4
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 3
- 239000012359 Methanesulfonyl chloride Substances 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 claims description 2
- RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 claims description 2
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 claims 2
- 125000003396 thiol group Chemical class [H]S* 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 abstract description 3
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 125000001188 haloalkyl group Chemical group 0.000 abstract 1
- 239000011541 reaction mixture Substances 0.000 description 10
- 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
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- MCTWTZJPVLRJOU-UHFFFAOYSA-N 1-methyl-1H-imidazole Chemical compound CN1C=CN=C1 MCTWTZJPVLRJOU-UHFFFAOYSA-N 0.000 description 2
- HPYNZHMRTTWQTB-UHFFFAOYSA-N 2,3-dimethylpyridine Chemical compound CC1=CC=CN=C1C HPYNZHMRTTWQTB-UHFFFAOYSA-N 0.000 description 2
- BWZVCCNYKMEVEX-UHFFFAOYSA-N 2,4,6-Trimethylpyridine Chemical compound CC1=CC(C)=NC(C)=C1 BWZVCCNYKMEVEX-UHFFFAOYSA-N 0.000 description 2
- JYYNAJVZFGKDEQ-UHFFFAOYSA-N 2,4-Dimethylpyridine Chemical compound CC1=CC=NC(C)=C1 JYYNAJVZFGKDEQ-UHFFFAOYSA-N 0.000 description 2
- NUHFJFXYAKTQLZ-UHFFFAOYSA-N 2-methyl-3-methylsulfonyl-4-(trifluoromethyl)benzoic acid Chemical compound CC1=C(C(O)=O)C=CC(C(F)(F)F)=C1S(C)(=O)=O NUHFJFXYAKTQLZ-UHFFFAOYSA-N 0.000 description 2
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 2
- NURQLCJSMXZBPC-UHFFFAOYSA-N 3,4-dimethylpyridine Chemical compound CC1=CC=NC=C1C NURQLCJSMXZBPC-UHFFFAOYSA-N 0.000 description 2
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
- FKNQCJSGGFJEIZ-UHFFFAOYSA-N 4-methylpyridine Chemical compound CC1=CC=NC=C1 FKNQCJSGGFJEIZ-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methylaniline Chemical compound CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- 150000001558 benzoic acid derivatives Chemical class 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 230000002363 herbicidal effect Effects 0.000 description 2
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- LZDKZFUFMNSQCJ-UHFFFAOYSA-N 1,2-diethoxyethane Chemical compound CCOCCOCC LZDKZFUFMNSQCJ-UHFFFAOYSA-N 0.000 description 1
- VZXTWGWHSMCWGA-UHFFFAOYSA-N 1,3,5-triazine-2,4-diamine Chemical compound NC1=NC=NC(N)=N1 VZXTWGWHSMCWGA-UHFFFAOYSA-N 0.000 description 1
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- AOPDRZXCEAKHHW-UHFFFAOYSA-N 1-pentoxypentane Chemical compound CCCCCOCCCCC AOPDRZXCEAKHHW-UHFFFAOYSA-N 0.000 description 1
- MXVMRHIWTSFDPU-UHFFFAOYSA-N 2-chlorobenzenecarboximidamide Chemical class NC(=N)C1=CC=CC=C1Cl MXVMRHIWTSFDPU-UHFFFAOYSA-N 0.000 description 1
- XWKFPIODWVPXLX-UHFFFAOYSA-N 2-methyl-5-methylpyridine Natural products CC1=CC=C(C)N=C1 XWKFPIODWVPXLX-UHFFFAOYSA-N 0.000 description 1
- ICGLPKIVTVWCFT-UHFFFAOYSA-N 4-methylbenzenesulfonohydrazide Chemical compound CC1=CC=C(S(=O)(=O)NN)C=C1 ICGLPKIVTVWCFT-UHFFFAOYSA-N 0.000 description 1
- 241000254032 Acrididae Species 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
- WXIUBYCJAAEOFL-UHFFFAOYSA-N [S].ClOCl Chemical compound [S].ClOCl WXIUBYCJAAEOFL-UHFFFAOYSA-N 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- KVNRLNFWIYMESJ-UHFFFAOYSA-N butyronitrile Chemical compound CCCC#N KVNRLNFWIYMESJ-UHFFFAOYSA-N 0.000 description 1
- OWIUPIRUAQMTTK-UHFFFAOYSA-N carbazic acid Chemical compound NNC(O)=O OWIUPIRUAQMTTK-UHFFFAOYSA-N 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 229950005499 carbon tetrachloride Drugs 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- LFKYBJLFJOOKAE-UHFFFAOYSA-N imidazol-2-ylidenemethanone Chemical compound O=C=C1N=CC=N1 LFKYBJLFJOOKAE-UHFFFAOYSA-N 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-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
- LRDFRRGEGBBSRN-UHFFFAOYSA-N isobutyronitrile Chemical compound CC(C)C#N LRDFRRGEGBBSRN-UHFFFAOYSA-N 0.000 description 1
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 1
- 229940011051 isopropyl acetate Drugs 0.000 description 1
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000010667 large scale reaction Methods 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 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
- 238000003756 stirring Methods 0.000 description 1
- FWMUJAIKEJWSSY-UHFFFAOYSA-N sulfur dichloride Chemical compound ClSCl FWMUJAIKEJWSSY-UHFFFAOYSA-N 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
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
- C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
- C07D271/10—1,3,4-Oxadiazoles; Hydrogenated 1,3,4-oxadiazoles
- C07D271/113—1,3,4-Oxadiazoles; Hydrogenated 1,3,4-oxadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/82—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with three ring hetero atoms
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/582—Recycling of unreacted starting or intermediate materials
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Shaping By String And By Release Of Stress In Plastics And The Like (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Laminated Bodies (AREA)
Abstract
本發明闡述製備下式(I)之N-(1,3,4-□二唑-2-基)芳基甲醯胺之方法□。 其中之取代基係諸如氫、烷基、鹵烷基或芳基之基團。
Description
本發明係關於製備具除草活性之N-(1,3,4-二唑-2-基)芳基甲醯胺之方法。
WO 2012/126932 A1揭示具除草活性之N-(1,3,4-二唑-2-基)芳基甲醯胺。其製備方法亦闡述於其中。在此方法中，經取代之苯甲酸與在5位上經取代之2-胺基-1,3,4-二唑在活化試劑(例如羰基咪唑(CDI)、二環己基碳二亞胺或2,4,6-三丙基-1,3,5,2,4,6-三氧雜三磷雜環己烷-2,4,6-三氧化物)之存在下反應。然而，此等試劑不適於大規模之反應，此乃因其昂貴且不能重複使用。自Zhur.Org Khim.V.25, N. 10, 1989, 2216得知，經取代之苯甲醯氯與2-胺基-1,3,4-二唑反應不僅得到期望之2-苯甲醯基胺基-1,3,4-二唑，亦得到異構物3-苯甲醯基-2-亞胺基-1,3,4-二唑啉。
本發明之目標係提供製備N-(1,3,4-二唑-2-基)芳基甲醯胺之方法，其克服自先前技術得知之方法的缺點。 現已發現N-(1,3,4-二唑-2-基)芳基甲醯胺可藉由經取代之苯甲酸與在5位上經取代之2-胺基-1,3,4-二唑在廉價的活化試劑與鹼之存在下反應而成本有效地且以高產率製備。 因此，本發明係關於藉由使通式(II)之2-胺基-1,3,4-二唑與通式(III)之苯甲酸反應來製備通式(I)之N-(1,3,4-二唑-2-基)芳基甲醯胺之方法， 其特徵在於該方法係於以下情形下實施： a)在來自由以下組成之群之活化試劑(活化劑)之存在下：亞硫醯氯、光氣、雙光氣、甲磺醯氯、對甲苯磺醯氯、POCl3
、PCl5
、草醯氯及C1
-C8
-烷基-OC(O)Cl，以及 (b)在通式(IV)之鹼之存在下，及 c)其中取代基係如下文所定義： R1
係氫、C3
-C12
-環烷基、C1
-C8
-烷基、C1
-C5
-烷氧基、鹵素、氰基或苯基， R2
係氫、C1
-C5
-烷基或鹵素， R3
係氫、C1
-C8
-烷基、C1
-C8
-烷基硫基、C1
-C8
-烷基亞磺醯基或C1
-C8
-烷基磺醯基， R4
係C1
-C5
-烷基或C1
-C3
-鹵烷基， R5
係C1
-C12
-烷基或苯基。 本發明方法之關鍵優點係高產率、使用廉價試劑及可重複使用式(IV)之鹼。 式(III)之經取代之苯甲酸係自例如WO 2012/126932 A1得知。式(II)之2-胺基-1,3,4-二唑可自市面購得或可藉由例如Tetrahedron, 69, 2013 2075-2080中所述之方法自羧醯肼製備。式(IV)之鹼同樣可自市面購得或可藉由熟習此項技術者已知之方法獲得。 在式(I)、(II)、(III)及(IV)中，具有多於兩個碳原子之烷基可係直鏈或具支鏈。烷基係(例如)甲基、乙基、正丙基或異丙基、正丁基、異丁基、第三丁基或2-丁基、戊基、己基(例如正己基、異己基及1,3-二甲基丁基)。此同樣適用於烷氧基及環烷基。 鹵素係氟、氯、溴或碘，較佳地氟或氯。 若基團(group)經多個基團(radical)多取代，則此應理解為意指此基團(group)經一或多個選自所提及之相同或不同基團(radical)取代。 式(II)及(III)之化合物通常以0.8至1.5之莫耳比使用。式(II)化合物較佳以相對於式(III)化合物過量10%使用。 活化劑及式(III)化合物通常以0.5至3、較佳1至2、尤佳地1.2至1.9之莫耳比使用。 所使用之活化劑較佳係亞硫醯氯、光氣或雙光氣，尤佳地亞硫醯氯。 式(IV)之鹼及式(III)化合物通常以0.5至10、較佳地1至3、尤佳地1至2.5之莫耳比使用。 本發明之方法通常於溶劑中實施。適宜溶劑係惰性有機溶劑，較佳地脂肪族、脂環族或芳香族烴，例如石油醚、己烷、庚烷、環己烷、甲基環己烷、苯、甲苯、二甲苯及十氫萘；鹵化烴，例如氯苯、二氯苯、二氯甲烷、氯仿、四氯甲烷、二氯乙烷及三氯乙烷；酯，例如乙酸乙酯及乙酸異丙酯；醚，例如二乙醚、二異丙醚、甲基第三丁基醚、甲基第三戊基醚、二烷、四氫呋喃、1,2-二甲氧基乙烷、1,2-二乙氧基乙烷及大茴香醚；酮，例如丙酮、丁酮、甲基異丁基酮及環己酮；腈，例如乙腈、丙腈、正丁腈或異丁腈及苯甲腈；醯胺，例如N,N-二甲基甲醯胺、N,N-二甲基乙醯胺、N-甲基甲醯苯胺、N-甲基吡咯啶酮及六甲基磷醯胺；吡啶，例如2-甲基吡啶、3-甲基吡啶、4-甲基吡啶、2,3-二甲基吡啶、2-甲基-5-乙基吡啶、2,6-二甲基吡啶、2,4-二甲基吡啶、3,4-二甲基吡啶及2,4,6-三甲基吡啶。上述溶劑之混合物亦係適宜的。 本發明方法中所使用之溶劑較佳係四氫呋喃、乙腈、3-甲基吡啶或2-甲基-5-乙基吡啶。尤佳者係3-甲基吡啶。 本發明之方法通常於-5℃至50℃、較佳0℃至25℃之溫度範圍內實施。 通常實施本發明之方法使得將式(II)、(III)及(IV)化合物加載於溶劑中且活化劑係在攪拌的同時逐滴緩慢添加或在使用光氣的情況下將其引入。反應之進程可藉由HPLC監測。反應通常在10小時至20小時後完成。 反應完成後，將反應混合物冷卻且產物通常幾乎定量地沈澱出。或者，可利用極性溶劑(例如水或醇，例如異丙醇)稀釋反應混合物。式(I)之反應產物以高純度獲得，且若需要可進一步純化。在20℃與35℃間之溫度下經3小時至6小時將水添加至反應混合物係特別有利的。在此情況下，獲得呈快速可濾過形式產物。母液利用氫氧化鈉水溶液處理後，可藉由蒸餾回收約95%之式(IV)之鹼。 本發明之方法較佳利用式(II)及(III)之化合物實施，其中 R1
係氫、甲基、乙基、正丙基、異丙基或苯基， R2
係甲基或氯， R3
係甲基硫基、甲基亞磺醯基或甲基磺醯基， R4
係三氟甲基， R5
係甲基或正丁基。 本發明之方法尤佳利用式(II)及(III)之化合物實施，其中 R1
係甲基， R2
係甲基或氯， R3
係甲基磺醯基， R4
係三氟甲基， R5
係甲基。 後續之製備實例更特別地闡明本發明。 2-甲基-N-(5-甲基-1,3,4-二唑-2-基)-3-(甲基磺醯基)-4-(三氟甲基)苯甲醯胺(變化形式1)之製備 將57 g (200 mmol) 2-甲基-3-甲基磺醯基-4-三氟甲基苯甲酸、21.8 g (220 mmol) 2-胺基-5-甲基-1,3,4-二唑及32.8 g (400 mmol) N-甲基咪唑溶解於300 ml 3-甲基吡啶中並攪拌30分鐘。冷卻至10℃後，經60分鐘逐滴添加38.2 g (320 mmol)亞硫醯氯，使反應混合物之溫度保持在10℃與20℃之間。然後在20℃下將反應混合物再攪拌18小時。然後經30分鐘逐滴添加200 ml水使得反應混合物之溫度保持在25℃與30℃之間。在40℃至45℃下攪拌反應混合物4小時並冷卻至20℃。過濾後，用200 ml水及100 ml 5%鹽酸洗滌產物。將殘留物乾燥後，獲得62.4 g 2-甲基-N-(5-甲基-1,3,4-二唑-2-基)-3-(甲基磺醯基)-4-(三氟甲基)苯甲醯胺(產率86%)。 2-甲基-N-(5-甲基-1,3,4-二唑-2-基)-3-(甲基磺醯基)-4-(三氟甲基)苯甲醯胺(變化形式2)之製備 將57 g (200 mmol) 2-甲基-3-甲基磺醯基-4-三氟甲基苯甲酸、21.8 g (220 mmol) 2-胺基-5-甲基-1,3,4-二唑及32.8 g (400 mmol) N-甲基咪唑溶解於300 ml 3-甲基吡啶中並攪拌30分鐘。冷卻至10℃後，經60分鐘逐滴添加38.2 g (320 mmol)亞硫醯氯使得反應混合物之溫度保持在10℃與20℃之間。然後在20℃下攪拌反應混合物18小時。然後經6小時逐滴添加200 ml水使得反應混合物之溫度保持在25℃與30℃之間。將所得懸浮液冷卻至15℃，過濾並利用200 ml水及100 ml 5%鹽酸洗滌濾餅。將殘留物乾燥後，獲得65.5 g 2-甲基-N-(5-甲基-1,3,4-二唑-2-基)-3-(甲基磺醯基)-4-(三氟甲基)苯甲醯胺(產率90%)。 出於比較目的，在其他條件及化學計量比相同之情形下，使用自WO 2012/126932 A1得知之草醯氯(代替亞硫醯氯)及4-二甲基胺基吡啶(代替N-甲基咪唑)之試劑實施上述反應。此獲得11.1 g 2-甲基-N-(5-甲基-1,3,4-二唑-2-基)-3-(甲基磺醯基)-4-(三氟甲基)苯甲醯胺(產率15%)。
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Claims (11)
- 一種製備式(I)之N-(1,3,4-二唑-2-基)芳基甲醯胺之方法，該方法藉由使式(II)之2-胺基-1,3,4-二唑與式(III)之苯甲酸反應來實施， 其特徵在於該方法係於以下情形下實施 a)在來自由以下組成之群之活化試劑之存在下：亞硫醯氯、光氣、雙光氣、甲磺醯氯、對甲苯磺醯氯、POCl3 、PCl5 、草醯氯及C1 -C8 -烷基-OC(O)Cl，以及 (b)在通式(IV)之鹼之存在下，及 c)其中取代基係如下文所定義： R1 係氫、C3 -C12 -環烷基、C1 -C8 -烷基、C1 -C5 -烷氧基、鹵素、氰基或苯基， R2 係氫、C1 -C5 -烷基或鹵素， R3 係氫、C1 -C8 -烷基、C1 -C8 -烷基硫基、C1 -C8 -烷基亞磺醯基或C1 -C8 -烷基磺醯基， R4 係C1 -C5 -烷基或C1 -C3 -鹵烷基， R5 係C1 -C12 -烷基或苯基。
- 如請求項1之方法，其中該式(II)化合物係以相對於該式(III)化合物過量10%使用。
- 如請求項1之方法，其中使用亞硫醯氯、光氣或雙光氣作為活化劑。
- 如請求項1之方法，其中使用亞硫醯氯作為活化劑。
- 如請求項1之方法，其中該活化劑及該式(III)化合物係以1.2至1.9之莫耳比使用。
- 如請求項1之方法，其中該式(IV)之鹼及該式(III)化合物係以1至2.5之莫耳比使用。
- 如請求項1之方法，其中所使用之溶劑係四氫呋喃、乙腈、2-甲基-5-乙基吡啶或3-甲基吡啶。
- 如請求項1之方法，其中所使用之溶劑係3-甲基吡啶。
- 如請求項1之方法，其中 R1 係氫、甲基、乙基、正丙基、異丙基或苯基， R2 係甲基或氯， R3 係甲基硫基、甲基亞磺醯基或甲基磺醯基， R4 係三氟甲基， R5 係甲基或正丁基。
- 如請求項1之方法，其中 R1 係甲基， R2 係甲基或氯， R3 係甲基磺醯基， R4 係三氟甲基， R5 係甲基。
- 如請求項1之方法，其中該反應係在0℃至25℃之範圍內實施。
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| JP2009091267A (ja) * | 2007-10-04 | 2009-04-30 | Kyorin Pharmaceut Co Ltd | アミド誘導体及びそれらを有効成分とするスフィンゴシン−１−リン酸−１（ｓ１ｐ１）受容体選択的アゴニスト |
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| HRP20161113T1 (hr) * | 2011-03-22 | 2016-12-02 | Bayer Intellectual Property Gmbh | N-(1,3,4-oksadiazol-2-il)arilkarboksamidi i njihova uporaba kao herbicida |
| BR112013024901A2 (pt) | 2011-03-28 | 2017-11-07 | Hoffmann La Roche | compostos de tiazolopirimidina |
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| MX2018003963A (es) | 2018-06-08 |
| BR112018006202A2 (pt) | 2018-10-09 |
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| JP2018529703A (ja) | 2018-10-11 |
| US20180273496A1 (en) | 2018-09-27 |
| IL258320A (en) | 2018-05-31 |
| US10189800B2 (en) | 2019-01-29 |
| KR20180059456A (ko) | 2018-06-04 |
| CN108137519A (zh) | 2018-06-08 |
| WO2017055175A1 (de) | 2017-04-06 |
| EP3356336A1 (de) | 2018-08-08 |
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