IE54064B1

IE54064B1 - Novel phenyl-substituted sulfonamides

Novel phenyl-substituted sulfonamides

Info

Publication number: IE54064B1
Authority: IE; Ireland
Prior art keywords: chj; och; ochj; compounds; compound
Prior art date: 1981-10-16

Application number

IE249182A

Other languages

English (en)

Other versions

IE822491L (en

Original Assignee

Du Pont

Priority date

1981-10-16

Filing date

1982-10-15

Publication date

1989-06-07

1982-08-11 Priority claimed from US06/406,191 external-priority patent/US4492596A/en

1982-10-15 Application filed by Du Pont filed Critical Du Pont

1983-04-16 Publication of IE822491L publication Critical patent/IE822491L/xx

1989-06-07 Publication of IE54064B1 publication Critical patent/IE54064B1/en

Links

-1 phenyl-substituted sulfonamides Chemical class 0.000 title claims description 68
150000001875 compounds Chemical class 0.000 claims abstract description 211
229910052717 sulfur Inorganic materials 0.000 claims abstract description 8
229910052760 oxygen Inorganic materials 0.000 claims abstract description 5
238000000034 method Methods 0.000 claims description 128
239000000203 mixture Substances 0.000 claims description 60
229910052801 chlorine Inorganic materials 0.000 claims description 59
229910052739 hydrogen Inorganic materials 0.000 claims description 57
125000000217 alkyl group Chemical group 0.000 claims description 49
229910052794 bromium Inorganic materials 0.000 claims description 48
229940124530 sulfonamide Drugs 0.000 claims description 39
239000007787 solid Substances 0.000 claims description 31
150000003456 sulfonamides Chemical class 0.000 claims description 30
150000001412 amines Chemical class 0.000 claims description 24
150000003839 salts Chemical class 0.000 claims description 20
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 19
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 19
230000012010 growth Effects 0.000 claims description 9
125000004432 carbon atom Chemical group C* 0.000 claims description 8
239000003085 diluting agent Substances 0.000 claims description 8
230000008635 plant growth Effects 0.000 claims description 7
239000004094 surface-active agent Substances 0.000 claims description 7
101100054666 Streptomyces halstedii sch3 gene Proteins 0.000 claims description 6
239000000010 aprotic solvent Substances 0.000 claims description 4
125000005605 benzo group Chemical group 0.000 claims description 4
GTCAXTIRRLKXRU-UHFFFAOYSA-N carbamic acid methyl ester Natural products COC(N)=O GTCAXTIRRLKXRU-UHFFFAOYSA-N 0.000 claims description 4
239000003795 chemical substances by application Substances 0.000 claims description 4
WZHRJGWXUCLILI-UHFFFAOYSA-N sulfonylcarbamic acid Chemical compound OC(=O)N=S(=O)=O WZHRJGWXUCLILI-UHFFFAOYSA-N 0.000 claims description 4
JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 claims description 4
239000007788 liquid Substances 0.000 claims description 3
QLDMFRAYUXNVSE-UHFFFAOYSA-N 1-(4,6-dimethoxypyrimidin-2-yl)-3-[(2-methyl-2,3-dihydro-1-benzofuran-7-yl)sulfonyl]urea Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)C=2C=3OC(C)CC=3C=CC=2)=N1 QLDMFRAYUXNVSE-UHFFFAOYSA-N 0.000 claims description 2
ROORDVPLFPIABK-UHFFFAOYSA-N diphenyl carbonate Chemical compound C=1C=CC=CC=1OC(=O)OC1=CC=CC=C1 ROORDVPLFPIABK-UHFFFAOYSA-N 0.000 claims description 2
231100001184 nonphytotoxic Toxicity 0.000 claims description 2
230000001276 controlling effect Effects 0.000 claims 3
GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 claims 1
125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims 1
JSVMZWXASRXRHZ-UHFFFAOYSA-N 2-methyl-1-benzofuran-7-sulfonamide Chemical compound CC1=CC2=C(O1)C(=CC=C2)S(N)(=O)=O JSVMZWXASRXRHZ-UHFFFAOYSA-N 0.000 claims 1
GGFJPYWUQCOYLQ-UHFFFAOYSA-N 4-methoxy-6-methylpyrimidine Chemical compound COC1=CC(C)=NC=N1 GGFJPYWUQCOYLQ-UHFFFAOYSA-N 0.000 claims 1
RPABXFDGXPYCCN-UHFFFAOYSA-N CC1=CC2=C(S1)C(=CC=C2)S(=O)(=O)N Chemical compound CC1=CC2=C(S1)C(=CC=C2)S(=O)(=O)N RPABXFDGXPYCCN-UHFFFAOYSA-N 0.000 claims 1
125000006519 CCH3 Chemical group 0.000 claims 1
101150065749 Churc1 gene Proteins 0.000 claims 1
102100038239 Protein Churchill Human genes 0.000 claims 1
XSXHWVKGUXMUQE-UHFFFAOYSA-N osmium dioxide Inorganic materials O=[Os]=O XSXHWVKGUXMUQE-UHFFFAOYSA-N 0.000 claims 1
230000001105 regulatory effect Effects 0.000 claims 1
230000002194 synthesizing effect Effects 0.000 claims 1
229910052736 halogen Inorganic materials 0.000 abstract description 2
150000002367 halogens Chemical class 0.000 abstract description 2
125000000962 organic group Chemical group 0.000 abstract 2
RAHZWNYVWXNFOC-UHFFFAOYSA-N sulfur dioxide Inorganic materials O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 304
239000000460 chlorine Substances 0.000 description 112
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 96
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 82
238000006243 chemical reaction Methods 0.000 description 67
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 60
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 56
235000007320 Avena fatua Nutrition 0.000 description 54
241000209140 Triticum Species 0.000 description 54
235000021307 Triticum Nutrition 0.000 description 54
244000075850 Avena orientalis Species 0.000 description 53
244000068988 Glycine max Species 0.000 description 53
235000010469 Glycine max Nutrition 0.000 description 53
235000005373 Uvularia sessilifolia Nutrition 0.000 description 53
244000277285 Cassia obtusifolia Species 0.000 description 52
235000006719 Cassia obtusifolia Nutrition 0.000 description 52
240000008042 Zea mays Species 0.000 description 52
235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 52
235000002017 Zea mays subsp mays Nutrition 0.000 description 52
235000005822 corn Nutrition 0.000 description 52
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 52
241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 51
235000014552 Cassia tora Nutrition 0.000 description 51
244000075634 Cyperus rotundus Species 0.000 description 51
240000007594 Oryza sativa Species 0.000 description 51
235000007164 Oryza sativa Nutrition 0.000 description 51
235000011684 Sorghum saccharatum Nutrition 0.000 description 51
235000021536 Sugar beet Nutrition 0.000 description 51
239000000543 intermediate Substances 0.000 description 51
235000009566 rice Nutrition 0.000 description 51
235000001602 Digitaria X umfolozi Nutrition 0.000 description 50
240000003176 Digitaria ciliaris Species 0.000 description 50
235000017898 Digitaria ciliaris Nutrition 0.000 description 50
235000005476 Digitaria cruciata Nutrition 0.000 description 50
235000006830 Digitaria didactyla Nutrition 0.000 description 50
235000005804 Digitaria eriantha ssp. eriantha Nutrition 0.000 description 50
235000010823 Digitaria sanguinalis Nutrition 0.000 description 50
235000014716 Eleusine indica Nutrition 0.000 description 50
241000209072 Sorghum Species 0.000 description 50
239000000243 solution Substances 0.000 description 50
235000005853 Cyperus esculentus Nutrition 0.000 description 49
241001506766 Xanthium Species 0.000 description 49
241000192043 Echinochloa Species 0.000 description 47
240000001549 Ipomoea eriocarpa Species 0.000 description 47
235000005146 Ipomoea eriocarpa Nutrition 0.000 description 47
239000002904 solvent Substances 0.000 description 39
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 35
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 34
229960000583 acetic acid Drugs 0.000 description 30
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 28
239000000725 suspension Substances 0.000 description 28
241001300479 Macroptilium Species 0.000 description 27
229920000742 Cotton Polymers 0.000 description 25
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 24
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 24
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 23
238000002360 preparation method Methods 0.000 description 23
239000000047 product Substances 0.000 description 22
238000006722 reduction reaction Methods 0.000 description 22
239000012442 inert solvent Substances 0.000 description 21
230000009467 reduction Effects 0.000 description 21
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 20
238000005481 NMR spectroscopy Methods 0.000 description 20
238000010438 heat treatment Methods 0.000 description 20
238000010992 reflux Methods 0.000 description 20
239000001257 hydrogen Substances 0.000 description 19
150000002828 nitro derivatives Chemical class 0.000 description 19
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 18
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 18
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
239000012954 diazonium Substances 0.000 description 17
150000001989 diazonium salts Chemical class 0.000 description 17
239000002585 base Substances 0.000 description 16
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 16
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 16
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 14
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 14
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 14
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 14
230000015572 biosynthetic process Effects 0.000 description 14
238000003786 synthesis reaction Methods 0.000 description 14
239000008187 granular material Substances 0.000 description 13
239000004615 ingredient Substances 0.000 description 13
238000007363 ring formation reaction Methods 0.000 description 13
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 13
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 12
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
150000002431 hydrogen Chemical class 0.000 description 12
239000000463 material Substances 0.000 description 12
239000003921 oil Substances 0.000 description 12
235000019198 oils Nutrition 0.000 description 12
YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 12
VFWCMGCRMGJXDK-UHFFFAOYSA-N 1-chlorobutane Chemical compound CCCCCl VFWCMGCRMGJXDK-UHFFFAOYSA-N 0.000 description 11
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 11
ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 11
QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 description 11
239000004009 herbicide Substances 0.000 description 11
229910052757 nitrogen Inorganic materials 0.000 description 11
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 10
239000003054 catalyst Substances 0.000 description 10
238000003756 stirring Methods 0.000 description 10
BUXTXUBQAKIQKS-UHFFFAOYSA-N sulfuryl diisocyanate Chemical class O=C=NS(=O)(=O)N=C=O BUXTXUBQAKIQKS-UHFFFAOYSA-N 0.000 description 10
XATYIBVSSKQMDX-UHFFFAOYSA-N 1-benzothiophen-7-amine Chemical class NC1=CC=CC2=C1SC=C2 XATYIBVSSKQMDX-UHFFFAOYSA-N 0.000 description 9
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 9
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
239000003153 chemical reaction reagent Substances 0.000 description 9
238000009472 formulation Methods 0.000 description 9
229920006395 saturated elastomer Polymers 0.000 description 9
229930192474 thiophene Natural products 0.000 description 9
HBEDSQVIWPRPAY-UHFFFAOYSA-N 2,3-dihydrobenzofuran Chemical compound C1=CC=C2OCCC2=C1 HBEDSQVIWPRPAY-UHFFFAOYSA-N 0.000 description 8
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 8
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 8
241000196324 Embryophyta Species 0.000 description 8
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 8
TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 8
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 8
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 8
239000012362 glacial acetic acid Substances 0.000 description 8
239000002245 particle Substances 0.000 description 8
235000010288 sodium nitrite Nutrition 0.000 description 8
239000007858 starting material Substances 0.000 description 8
239000008096 xylene Substances 0.000 description 8
YYWJHOJMCOIVNS-UHFFFAOYSA-N 1-benzofuran-7-amine Chemical class NC1=CC=CC2=C1OC=C2 YYWJHOJMCOIVNS-UHFFFAOYSA-N 0.000 description 7
UUFQTNFCRMXOAE-UHFFFAOYSA-N 1-methylmethylene Chemical compound C[CH] UUFQTNFCRMXOAE-UHFFFAOYSA-N 0.000 description 7
JCVKIWWAMUGSNB-UHFFFAOYSA-N 2,3-dihydro-1-benzothiophen-7-amine Chemical class NC1=CC=CC2=C1SCC2 JCVKIWWAMUGSNB-UHFFFAOYSA-N 0.000 description 7
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 7
101100167062 Caenorhabditis elegans chch-3 gene Proteins 0.000 description 7
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 7
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 7
239000002253 acid Substances 0.000 description 7
239000004480 active ingredient Substances 0.000 description 7
229960000892 attapulgite Drugs 0.000 description 7
230000000694 effects Effects 0.000 description 7
230000002363 herbicidal effect Effects 0.000 description 7
229910052943 magnesium sulfate Inorganic materials 0.000 description 7
235000019341 magnesium sulphate Nutrition 0.000 description 7
239000012074 organic phase Substances 0.000 description 7
230000001590 oxidative effect Effects 0.000 description 7
229910052625 palygorskite Inorganic materials 0.000 description 7
239000004563 wettable powder Substances 0.000 description 7
OCZGGFAZAPGFMC-UHFFFAOYSA-N 1-benzofuran-4-amine Chemical class NC1=CC=CC2=C1C=CO2 OCZGGFAZAPGFMC-UHFFFAOYSA-N 0.000 description 6
RWPLKRGISDOAAG-UHFFFAOYSA-N 2,3-dihydro-1-benzofuran-4-amine Chemical compound NC1=CC=CC2=C1CCO2 RWPLKRGISDOAAG-UHFFFAOYSA-N 0.000 description 6
QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 6
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 6
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 6
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 6
244000309464 bull Species 0.000 description 6
229910052799 carbon Inorganic materials 0.000 description 6
230000000850 deacetylating effect Effects 0.000 description 6
238000001914 filtration Methods 0.000 description 6
UJTMLNARSPORHR-UHFFFAOYSA-N oc2h5 Chemical compound C=C=[O+] UJTMLNARSPORHR-UHFFFAOYSA-N 0.000 description 6
229910000027 potassium carbonate Chemical class 0.000 description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 5
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 5
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
239000012267 brine Substances 0.000 description 5
150000004657 carbamic acid derivatives Chemical class 0.000 description 5
150000001732 carboxylic acid derivatives Chemical class 0.000 description 5
150000001768 cations Chemical class 0.000 description 5
238000004587 chromatography analysis Methods 0.000 description 5
238000001816 cooling Methods 0.000 description 5
229960003280 cupric chloride Drugs 0.000 description 5
238000003381 deacetylation reaction Methods 0.000 description 5
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 5
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
VGYWBWHGPATCBZ-UHFFFAOYSA-N methyl n-(4-methoxy-6-methylpyrimidin-2-yl)carbamate Chemical compound COC(=O)NC1=NC(C)=CC(OC)=N1 VGYWBWHGPATCBZ-UHFFFAOYSA-N 0.000 description 5
230000004048 modification Effects 0.000 description 5
238000012986 modification Methods 0.000 description 5
HNHVTXYLRVGMHD-UHFFFAOYSA-N n-butyl isocyanate Chemical compound CCCCN=C=O HNHVTXYLRVGMHD-UHFFFAOYSA-N 0.000 description 5
239000008188 pellet Substances 0.000 description 5
229920000137 polyphosphoric acid Polymers 0.000 description 5
150000003230 pyrimidines Chemical class 0.000 description 5
229910052708 sodium Inorganic materials 0.000 description 5
239000011734 sodium Substances 0.000 description 5
229910000104 sodium hydride Inorganic materials 0.000 description 5
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 5
239000000126 substance Substances 0.000 description 5
150000003918 triazines Chemical class 0.000 description 5
IRMXPESEXLQKHG-UHFFFAOYSA-N 1-benzothiophen-4-amine Chemical class NC1=CC=CC2=C1C=CS2 IRMXPESEXLQKHG-UHFFFAOYSA-N 0.000 description 4
UHHZGSLXPQGPJL-UHFFFAOYSA-N 2,3-dihydro-1-benzofuran-7-amine Chemical class NC1=CC=CC2=C1OCC2 UHHZGSLXPQGPJL-UHFFFAOYSA-N 0.000 description 4
TXFPEBPIARQUIG-UHFFFAOYSA-N 4'-hydroxyacetophenone Chemical compound CC(=O)C1=CC=C(O)C=C1 TXFPEBPIARQUIG-UHFFFAOYSA-N 0.000 description 4
KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical class NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 description 4
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 4
238000005727 Friedel-Crafts reaction Methods 0.000 description 4
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 4
UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 4
230000000397 acetylating effect Effects 0.000 description 4
239000007864 aqueous solution Substances 0.000 description 4
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RMAHPRNLQIRHIJ-UHFFFAOYSA-N methyl carbamimidate Chemical compound COC(N)=N RMAHPRNLQIRHIJ-UHFFFAOYSA-N 0.000 description 1
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GJANNTIFPQOAJM-UHFFFAOYSA-N n-(1-benzofuran-4-yl)acetamide Chemical compound CC(=O)NC1=CC=CC2=C1C=CO2 GJANNTIFPQOAJM-UHFFFAOYSA-N 0.000 description 1
OCAQMPIWVCVFTH-UHFFFAOYSA-N n-(2,3-dihydro-1-benzofuran-7-yl)acetamide Chemical compound CC(=O)NC1=CC=CC2=C1OCC2 OCAQMPIWVCVFTH-UHFFFAOYSA-N 0.000 description 1
ILSHVWZBVQAUNX-UHFFFAOYSA-N n-(2-methyl-2,3-dihydro-1-benzothiophen-7-yl)acetamide Chemical compound C1=CC(NC(C)=O)=C2SC(C)CC2=C1 ILSHVWZBVQAUNX-UHFFFAOYSA-N 0.000 description 1
CQEQGGWLBYIMLV-UHFFFAOYSA-N n-tert-butyl-2,2-dimethyl-3h-1-benzothiophene-7-sulfonamide Chemical compound CC(C)(C)NS(=O)(=O)C1=CC=CC2=C1SC(C)(C)C2 CQEQGGWLBYIMLV-UHFFFAOYSA-N 0.000 description 1
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230000017074 necrotic cell death Effects 0.000 description 1
230000000802 nitrating effect Effects 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
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239000005416 organic matter Substances 0.000 description 1
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238000004806 packaging method and process Methods 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
235000020030 perry Nutrition 0.000 description 1
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238000005191 phase separation Methods 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical compound O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 description 1
UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
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239000011591 potassium Substances 0.000 description 1
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LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
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238000001556 precipitation Methods 0.000 description 1
POSICDHOUBKJKP-UHFFFAOYSA-N prop-2-enoxybenzene Chemical compound C=CCOC1=CC=CC=C1 POSICDHOUBKJKP-UHFFFAOYSA-N 0.000 description 1
QGNRLAFFKKBSIM-UHFFFAOYSA-N prop-2-enylsulfanylbenzene Chemical compound C=CCSC1=CC=CC=C1 QGNRLAFFKKBSIM-UHFFFAOYSA-N 0.000 description 1
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RMBAVIFYHOYIFM-UHFFFAOYSA-M sodium methanethiolate Chemical compound [Na+].[S-]C RMBAVIFYHOYIFM-UHFFFAOYSA-M 0.000 description 1
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125000004434 sulfur atom Chemical group 0.000 description 1
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125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
238000010998 test method Methods 0.000 description 1
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VNNLHYZDXIBHKZ-UHFFFAOYSA-N thiophene-2-sulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CS1 VNNLHYZDXIBHKZ-UHFFFAOYSA-N 0.000 description 1
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YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
238000001665 trituration Methods 0.000 description 1
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229910052725 zinc Inorganic materials 0.000 description 1
QUEDXNHFTDJVIY-UHFFFAOYSA-N γ-tocopherol Chemical class OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1 QUEDXNHFTDJVIY-UHFFFAOYSA-N 0.000 description 1