NZ336992A - 3-heterocyclyl-substituted benzoyl derivatives - Google Patents

Info

Publication number

NZ336992A

NZ336992A NZ336992A NZ33699298A NZ336992A NZ 336992 A NZ336992 A NZ 336992A NZ 336992 A NZ336992 A NZ 336992A NZ 33699298 A NZ33699298 A NZ 33699298A NZ 336992 A NZ336992 A NZ 336992A

Authority

NZ

New Zealand

Prior art keywords

ibl

compounds

hydrogen

differ

fact

Prior art date

1997-01-17

Links

• Espacenet
• Global Dossier
• Discuss

• 125000003236 benzoyl group Chemical class [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 title abstract description 77
• 150000001875 compounds Chemical class 0.000 abstract description 582
• 239000001257 hydrogen Substances 0.000 abstract description 343
• 229910052739 hydrogen Inorganic materials 0.000 abstract description 343
• 229910052760 oxygen Inorganic materials 0.000 abstract description 45
• 238000000034 method Methods 0.000 abstract description 30
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract description 25
• 150000003839 salts Chemical class 0.000 abstract description 22
• 230000008569 process Effects 0.000 abstract description 19
• 125000001424 substituent group Chemical group 0.000 abstract description 14
• 229910052717 sulfur Inorganic materials 0.000 abstract description 12
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract description 9
• 239000004009 herbicide Substances 0.000 abstract description 6
• 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 abstract description 4
• 239000003795 chemical substances by application Substances 0.000 abstract description 4
• 125000003226 pyrazolyl group Chemical group 0.000 abstract description 4
• 239000000126 substance Substances 0.000 abstract description 2
• 239000013067 intermediate product Substances 0.000 abstract 1
• -1 Pyrazol-4-yl-benzoyl Chemical class 0.000 description 579
• 125000004435 hydrogen atom Chemical group [H]* 0.000 description 261
• 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 163
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 142
• 239000000460 chlorine Substances 0.000 description 135
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 107
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 103
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 72
• 239000000203 mixture Substances 0.000 description 65
• 150000002431 hydrogen Chemical class 0.000 description 57
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 54
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 54
• 125000006125 ethylsulfonyl group Chemical group 0.000 description 54
• 229910052736 halogen Inorganic materials 0.000 description 49
• 150000002367 halogens Chemical class 0.000 description 49
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 42
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 40
• 239000001301 oxygen Substances 0.000 description 40
• 239000000243 solution Substances 0.000 description 37
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 37
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 36
• 125000004093 cyano group Chemical group *C#N 0.000 description 36
• 229910052757 nitrogen Inorganic materials 0.000 description 36
• 229910052801 chlorine Inorganic materials 0.000 description 32
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 31
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 28
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 28
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
• 239000002904 solvent Substances 0.000 description 24
• 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 23
• 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 23
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 21
• 241001484259 Lacuna Species 0.000 description 20
• 239000004480 active ingredient Substances 0.000 description 20
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 20
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 19
• 241000196324 Embryophyta Species 0.000 description 19
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 18
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 18
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 17
• 238000005481 NMR spectroscopy Methods 0.000 description 17
• 229910052794 bromium Inorganic materials 0.000 description 17
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 17
• 125000000217 alkyl group Chemical group 0.000 description 16
• 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 16
• 125000006126 n-butyl sulfonyl group Chemical group 0.000 description 16
• 125000006124 n-propyl sulfonyl group Chemical group 0.000 description 16
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 15
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 15
• 150000002148 esters Chemical class 0.000 description 14
• 101100134925 Gallus gallus COR6 gene Proteins 0.000 description 13
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 13
• 101100054666 Streptomyces halstedii sch3 gene Proteins 0.000 description 13
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 13
• 230000002363 herbicidal effect Effects 0.000 description 13
• 239000002585 base Substances 0.000 description 12
• 125000001309 chloro group Chemical group Cl* 0.000 description 12
• 239000000047 product Substances 0.000 description 12
• FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 12
• 125000002887 hydroxy group Chemical group [H]O* 0.000 description 11
• 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 11
• 239000012074 organic phase Substances 0.000 description 11
• 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 description 11
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 10
• 101100167062 Caenorhabditis elegans chch-3 gene Proteins 0.000 description 10
• 238000006243 chemical reaction Methods 0.000 description 10
• JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 10
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 10
• 239000011737 fluorine Substances 0.000 description 10
• 229910052731 fluorine Inorganic materials 0.000 description 10
• 125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 description 10
• 239000003921 oil Substances 0.000 description 10
• 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 10
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
• OCBFFGCSTGGPSQ-UHFFFAOYSA-N [CH2]CC Chemical compound [CH2]CC OCBFFGCSTGGPSQ-UHFFFAOYSA-N 0.000 description 9
• 239000002253 acid Substances 0.000 description 9
• 150000001558 benzoic acid derivatives Chemical class 0.000 description 9
• 150000002825 nitriles Chemical class 0.000 description 9
• BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 8
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 8
• QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 8
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
• 239000008346 aqueous phase Substances 0.000 description 8
• 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 8
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
• 239000011541 reaction mixture Substances 0.000 description 8
• 238000005160 1H NMR spectroscopy Methods 0.000 description 7
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 7
• 239000006185 dispersion Substances 0.000 description 7
• PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 7
• 238000002360 preparation method Methods 0.000 description 7
• 238000010992 reflux Methods 0.000 description 7
• 239000007787 solid Substances 0.000 description 7
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 description 6
• WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 6
• IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 6
• 125000003545 alkoxy group Chemical group 0.000 description 6
• 235000010233 benzoic acid Nutrition 0.000 description 6
• 239000004359 castor oil Substances 0.000 description 6
• 235000019438 castor oil Nutrition 0.000 description 6
• 239000003054 catalyst Substances 0.000 description 6
• 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 6
• 239000012141 concentrate Substances 0.000 description 6
• 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 6
• 125000001153 fluoro group Chemical group F* 0.000 description 6
• 238000009472 formulation Methods 0.000 description 6
• ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 6
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Chemical group COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
• 239000007858 starting material Substances 0.000 description 6
• 239000000725 suspension Substances 0.000 description 6
• 238000003786 synthesis reaction Methods 0.000 description 6
• 238000012360 testing method Methods 0.000 description 6
• QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 5
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
• IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 5
• DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound 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 description 5
• VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 5
• 240000008042 Zea mays Species 0.000 description 5
• 150000001299 aldehydes Chemical class 0.000 description 5
• 229910000288 alkali metal carbonate Inorganic materials 0.000 description 5
• 150000008041 alkali metal carbonates Chemical class 0.000 description 5
• 125000004414 alkyl thio group Chemical group 0.000 description 5
• 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 5
• WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 5
• 229910021386 carbon form Inorganic materials 0.000 description 5
• 244000038559 crop plants Species 0.000 description 5
• 239000000839 emulsion Substances 0.000 description 5
• 230000007062 hydrolysis Effects 0.000 description 5
• 238000006460 hydrolysis reaction Methods 0.000 description 5
• 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 5
• CMHAHZIWNCFHFL-UHFFFAOYSA-N methyl 2-chloro-3-(4,5-dihydro-1,2-oxazol-3-yl)-4-methylsulfonylbenzoate Chemical compound COC(=O)C1=CC=C(S(C)(=O)=O)C(C=2CCON=2)=C1Cl CMHAHZIWNCFHFL-UHFFFAOYSA-N 0.000 description 5
• ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 5
• 150000003254 radicals Chemical class 0.000 description 5
• 239000000741 silica gel Substances 0.000 description 5
• 229910002027 silica gel Inorganic materials 0.000 description 5
• 239000011734 sodium Substances 0.000 description 5
• 229910052708 sodium Inorganic materials 0.000 description 5
• 239000001632 sodium acetate Substances 0.000 description 5
• 235000017281 sodium acetate Nutrition 0.000 description 5
• 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 description 5
• 238000011282 treatment Methods 0.000 description 5
• JURLTYXSZFLINT-UHFFFAOYSA-N 2-chloro-3-(4,5-dihydro-1,2-oxazol-3-yl)-4-methylsulfonylbenzoyl chloride Chemical compound CS(=O)(=O)C1=CC=C(C(Cl)=O)C(Cl)=C1C1=NOCC1 JURLTYXSZFLINT-UHFFFAOYSA-N 0.000 description 4
• RRFGGUXLGOVPOP-UHFFFAOYSA-N 2-chloro-3-methyl-4-methylsulfonylbenzoic acid Chemical compound CC1=C(Cl)C(C(O)=O)=CC=C1S(C)(=O)=O RRFGGUXLGOVPOP-UHFFFAOYSA-N 0.000 description 4
• RFONJRMUUALMBA-UHFFFAOYSA-N 2-methanidylpropane Chemical compound CC(C)[CH2-] RFONJRMUUALMBA-UHFFFAOYSA-N 0.000 description 4
• IUCXCDBYRBQAJD-UHFFFAOYSA-N CCN1N=CC(C(=O)C=2C(=C(C=3CCON=3)C(=CC=2)S(C)(=O)=O)Cl)=C1O Chemical compound CCN1N=CC(C(=O)C=2C(=C(C=3CCON=3)C(=CC=2)S(C)(=O)=O)Cl)=C1O IUCXCDBYRBQAJD-UHFFFAOYSA-N 0.000 description 4
• FCODLBLEKSFOLV-UHFFFAOYSA-N CN1N=CC(C(=O)C=2C(=C(C=3CCON=3)C(=CC=2)S(C)(=O)=O)Cl)=C1O Chemical compound CN1N=CC(C(=O)C=2C(=C(C=3CCON=3)C(=CC=2)S(C)(=O)=O)Cl)=C1O FCODLBLEKSFOLV-UHFFFAOYSA-N 0.000 description 4
• PYKSVIGIFCAYLQ-UHFFFAOYSA-N Cc1nn(C)c(O)c1C(=O)c1ccc(c(C2=NC(=O)C(=O)S2)c1Cl)S(C)(=O)=O Chemical compound Cc1nn(C)c(O)c1C(=O)c1ccc(c(C2=NC(=O)C(=O)S2)c1Cl)S(C)(=O)=O PYKSVIGIFCAYLQ-UHFFFAOYSA-N 0.000 description 4
• XPEXBVSNMZHFFO-UHFFFAOYSA-N ClC1=C(C(=O)Cl)C=CC(=C1C(=O)NCC(CCl)C)S(=O)(=O)C Chemical compound ClC1=C(C(=O)Cl)C=CC(=C1C(=O)NCC(CCl)C)S(=O)(=O)C XPEXBVSNMZHFFO-UHFFFAOYSA-N 0.000 description 4
• XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 4
• ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 4
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 4
• PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 4
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 4
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
• 229910052783 alkali metal Inorganic materials 0.000 description 4
• 150000001448 anilines Chemical class 0.000 description 4
• 150000001559 benzoic acids Chemical class 0.000 description 4
• 150000001735 carboxylic acids Chemical class 0.000 description 4
• MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
• 238000001816 cooling Methods 0.000 description 4
• IPZJQDSFZGZEOY-UHFFFAOYSA-N dimethylmethylene Chemical compound C[C]C IPZJQDSFZGZEOY-UHFFFAOYSA-N 0.000 description 4
• 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 4
• 239000008187 granular material Substances 0.000 description 4
• 125000004995 haloalkylthio group Chemical group 0.000 description 4
• 125000000623 heterocyclic group Chemical group 0.000 description 4
• 239000000543 intermediate Substances 0.000 description 4
• 235000012054 meals Nutrition 0.000 description 4
• GQERJGZVBMLHLP-UHFFFAOYSA-N methyl 2-chloro-3-(4,5-dihydro-1,3-oxazol-2-yl)-4-methylsulfonylbenzoate Chemical compound COC(=O)C1=CC=C(S(C)(=O)=O)C(C=2OCCN=2)=C1Cl GQERJGZVBMLHLP-UHFFFAOYSA-N 0.000 description 4
• GTXHAHDFJJTAKY-UHFFFAOYSA-N methyl 3-carbonochloridoyl-2-chloro-4-methylsulfonylbenzoate Chemical compound COC(=O)C1=CC=C(S(C)(=O)=O)C(C(Cl)=O)=C1Cl GTXHAHDFJJTAKY-UHFFFAOYSA-N 0.000 description 4
• 229910052763 palladium Inorganic materials 0.000 description 4
• 239000012071 phase Substances 0.000 description 4
• 229910000027 potassium carbonate Inorganic materials 0.000 description 4
• 239000000843 powder Substances 0.000 description 4
• 239000002244 precipitate Substances 0.000 description 4
• 229910000029 sodium carbonate Inorganic materials 0.000 description 4
• 239000011593 sulfur Substances 0.000 description 4
• RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 4
• 229910052727 yttrium Inorganic materials 0.000 description 4
• ZSHNSXSONOHWNB-UHFFFAOYSA-N 1-(2-chloro-3-methyl-4-methylsulfanylphenyl)ethanone Chemical compound CSC1=CC=C(C(C)=O)C(Cl)=C1C ZSHNSXSONOHWNB-UHFFFAOYSA-N 0.000 description 3
• WPWHSFAFEBZWBB-UHFFFAOYSA-N 1-butyl radical Chemical compound [CH2]CCC WPWHSFAFEBZWBB-UHFFFAOYSA-N 0.000 description 3
• YUTLRRXZEZXEAY-UHFFFAOYSA-N 2-chloro-3-(4,5-dihydro-1,2-oxazol-3-yl)-4-methylsulfonylbenzoic acid Chemical compound CS(=O)(=O)C1=CC=C(C(O)=O)C(Cl)=C1C1=NOCC1 YUTLRRXZEZXEAY-UHFFFAOYSA-N 0.000 description 3
• QRPLOBYIGXQKIO-UHFFFAOYSA-N 2-chloro-3-(5-methyl-4,5-dihydro-1,2-oxazol-3-yl)-4-methylsulfonylbenzoic acid Chemical compound O1C(C)CC(C=2C(=CC=C(C=2Cl)C(O)=O)S(C)(=O)=O)=N1 QRPLOBYIGXQKIO-UHFFFAOYSA-N 0.000 description 3
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
• QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 3
• PXVQWKUYBMZLRB-UHFFFAOYSA-N CC1=NN(C)C(O)=C1C(=O)C1=CC=C(S(C)(=O)=O)C(C=2SCCN=2)=C1Cl Chemical compound CC1=NN(C)C(O)=C1C(=O)C1=CC=C(S(C)(=O)=O)C(C=2SCCN=2)=C1Cl PXVQWKUYBMZLRB-UHFFFAOYSA-N 0.000 description 3
• VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 3
• 239000005977 Ethylene Substances 0.000 description 3
• WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
• PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 3
• WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 3
• 238000000297 Sandmeyer reaction Methods 0.000 description 3
• 241000209140 Triticum Species 0.000 description 3
• 235000021307 Triticum Nutrition 0.000 description 3
• 235000002017 Zea mays subsp mays Nutrition 0.000 description 3
• 150000007513 acids Chemical class 0.000 description 3
• 239000013543 active substance Substances 0.000 description 3
• 125000004644 alkyl sulfinyl group Chemical group 0.000 description 3
• 125000004390 alkyl sulfonyl group Chemical group 0.000 description 3
• 150000003863 ammonium salts Chemical class 0.000 description 3
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