JP2003503398A - 置換尿素 - Google Patents

Info

Publication number

JP2003503398A

JP2003503398A JP2001507011A JP2001507011A JP2003503398A JP 2003503398 A JP2003503398 A JP 2003503398A JP 2001507011 A JP2001507011 A JP 2001507011A JP 2001507011 A JP2001507011 A JP 2001507011A JP 2003503398 A JP2003503398 A JP 2003503398A

Authority

JP

Japan

Prior art keywords

alkyl

alkoxy

hydrogen

carbonyl

haloalkyl

Prior art date

1999-06-24

Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)

Withdrawn

Links

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• 150000003672 ureas Chemical class 0.000 title claims abstract description 47
• 239000004202 carbamide Substances 0.000 title claims description 45
• 150000001875 compounds Chemical class 0.000 claims abstract description 236
• 239000000203 mixture Substances 0.000 claims abstract description 70
• 235000013877 carbamide Nutrition 0.000 claims abstract description 62
• 238000000034 method Methods 0.000 claims abstract description 22
• 229910052727 yttrium Inorganic materials 0.000 claims abstract description 17
• 239000004009 herbicide Substances 0.000 claims abstract description 8
• -1 carbonylthio Chemical group 0.000 claims description 1355
• 229910052739 hydrogen Inorganic materials 0.000 claims description 210
• 239000001257 hydrogen Substances 0.000 claims description 209
• 239000000126 substance Substances 0.000 claims description 206
• 229910052736 halogen Inorganic materials 0.000 claims description 165
• 150000002367 halogens Chemical class 0.000 claims description 165
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 157
• 150000002431 hydrogen Chemical class 0.000 claims description 148
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 132
• 239000000460 chlorine Substances 0.000 claims description 131
• 125000001424 substituent group Chemical group 0.000 claims description 114
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 91
• 229910052760 oxygen Inorganic materials 0.000 claims description 80
• 125000003545 alkoxy group Chemical group 0.000 claims description 72
• 125000000217 alkyl group Chemical group 0.000 claims description 68
• 229910052717 sulfur Inorganic materials 0.000 claims description 61
• 125000005708 carbonyloxy group Chemical group [*:2]OC([*:1])=O 0.000 claims description 59
• 229910052801 chlorine Inorganic materials 0.000 claims description 57
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 54
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 51
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 44
• 125000000623 heterocyclic group Chemical group 0.000 claims description 44
• 239000001301 oxygen Substances 0.000 claims description 42
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 41
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 38
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 34
• 229910052731 fluorine Inorganic materials 0.000 claims description 32
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 29
• 239000011737 fluorine Substances 0.000 claims description 29
• 241000196324 Embryophyta Species 0.000 claims description 23
• 125000001188 haloalkyl group Chemical group 0.000 claims description 23
• 229920006395 saturated elastomer Polymers 0.000 claims description 22
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 21
• 229910052757 nitrogen Inorganic materials 0.000 claims description 21
• 150000003839 salts Chemical class 0.000 claims description 21
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 20
• 239000011593 sulfur Substances 0.000 claims description 20
• 229910052799 carbon Inorganic materials 0.000 claims description 17
• 125000003342 alkenyl group Chemical group 0.000 claims description 16
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 15
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 14
• 125000003302 alkenyloxy group Chemical group 0.000 claims description 14
• 125000000304 alkynyl group Chemical group 0.000 claims description 14
• 230000002363 herbicidal effect Effects 0.000 claims description 14
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 14
• 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 13
• 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 claims description 13
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 12
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 10
• 125000005842 heteroatom Chemical group 0.000 claims description 10
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 10
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 9
• 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 8
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 8
• 125000004076 pyridyl group Chemical group 0.000 claims description 8
• 125000005108 alkenylthio group Chemical group 0.000 claims description 7
• 150000003254 radicals Chemical class 0.000 claims description 7
• 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 6
• 125000002947 alkylene group Chemical group 0.000 claims description 6
• 125000002344 aminooxy group Chemical group [H]N([H])O[*] 0.000 claims description 6
• 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 6
• 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 6
• 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 6
• 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 claims description 6
• 125000005336 allyloxy group Chemical group 0.000 claims description 5
• CMWTZPSULFXXJA-VIFPVBQESA-N naproxen Chemical group C1=C([C@H](C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-VIFPVBQESA-N 0.000 claims description 5
• 230000036186 satiety Effects 0.000 claims description 5
• 235000019627 satiety Nutrition 0.000 claims description 5
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 5
• 125000003396 thiol group Chemical class [H]S* 0.000 claims description 5
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
• 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 4
• 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 4
• 125000004434 sulfur atom Chemical group 0.000 claims description 4
• SCVJRXQHFJXZFZ-KVQBGUIXSA-N 2-amino-9-[(2r,4s,5r)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-3h-purine-6-thione Chemical compound C1=2NC(N)=NC(=S)C=2N=CN1[C@H]1C[C@H](O)[C@@H](CO)O1 SCVJRXQHFJXZFZ-KVQBGUIXSA-N 0.000 claims description 3
• 241001553014 Myrsine salicina Species 0.000 claims description 3
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 3
• 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 3
• 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 3
• 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 3
• 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 3
• 150000001721 carbon Chemical group 0.000 claims description 3
• 229930002875 chlorophyll Natural products 0.000 claims description 3
• 235000019804 chlorophyll Nutrition 0.000 claims description 3
• ATNHDLDRLWWWCB-AENOIHSZSA-M chlorophyll a Chemical compound C1([C@@H](C(=O)OC)C(=O)C2=C3C)=C2N2C3=CC(C(CC)=C3C)=[N+]4C3=CC3=C(C=C)C(C)=C5N3[Mg-2]42[N+]2=C1[C@@H](CCC(=O)OC\C=C(/C)CCC[C@H](C)CCC[C@H](C)CCCC(C)C)[C@H](C)C2=C5 ATNHDLDRLWWWCB-AENOIHSZSA-M 0.000 claims description 3
• 125000004663 dialkyl amino group Chemical group 0.000 claims description 3
• 125000001841 imino group Chemical group [H]N=* 0.000 claims description 3
• 150000002829 nitrogen Chemical class 0.000 claims description 3
• 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 3
• 125000005493 quinolyl group Chemical group 0.000 claims description 3
• 125000003003 spiro group Chemical group 0.000 claims description 3
• 125000005102 carbonylalkoxy group Chemical group 0.000 claims description 2
• 125000005291 haloalkenyloxy group Chemical group 0.000 claims description 2
• 229940060942 methylin Drugs 0.000 claims description 2
• 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 claims description 2
• 125000003884 phenylalkyl group Chemical group 0.000 claims description 2
• 125000006493 trifluoromethyl benzyl group Chemical group 0.000 claims description 2
• 235000001508 sulfur Nutrition 0.000 claims 8
• 229910052770 Uranium Inorganic materials 0.000 claims 1
• 125000004429 atom Chemical group 0.000 claims 1
• 239000012752 auxiliary agent Substances 0.000 claims 1
• 125000004432 carbon atom Chemical group C* 0.000 claims 1
• 229940125890 compound Ia Drugs 0.000 description 135
• 238000006243 chemical reaction Methods 0.000 description 75
• XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 58
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 51
• WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 49
• 239000002253 acid Substances 0.000 description 46
• 239000002904 solvent Substances 0.000 description 45
• SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 description 38
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 35
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 28
• 238000003756 stirring Methods 0.000 description 21
• 229910000272 alkali metal oxide Inorganic materials 0.000 description 20
• 239000002585 base Substances 0.000 description 20
• 239000007858 starting material Substances 0.000 description 20
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 19
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 19
• 229910052794 bromium Inorganic materials 0.000 description 19
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 17
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 17
• 125000006367 bivalent amino carbonyl group Chemical group [H]N([*:1])C([*:2])=O 0.000 description 16
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 15
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
• MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 14
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 12
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 12
• 230000003647 oxidation Effects 0.000 description 12
• 238000007254 oxidation reaction Methods 0.000 description 12
• 150000003462 sulfoxides Chemical class 0.000 description 12
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 11
• 239000007800 oxidant agent Substances 0.000 description 11
• 239000000243 solution Substances 0.000 description 11
• NCJXHPIYRWIILF-UHFFFAOYSA-N 1h-triazole-4,5-dione Chemical class OC1=NN=NC1=O NCJXHPIYRWIILF-UHFFFAOYSA-N 0.000 description 10
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
• JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 10
• 239000012948 isocyanate Substances 0.000 description 10
• 150000002513 isocyanates Chemical class 0.000 description 10
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 10
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 9
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
• 150000001340 alkali metals Chemical class 0.000 description 9
• 239000003054 catalyst Substances 0.000 description 9
• 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 9
• 239000003921 oil Substances 0.000 description 9
• 150000003457 sulfones Chemical class 0.000 description 9
• 229930040373 Paraformaldehyde Natural products 0.000 description 8
• 150000007513 acids Chemical class 0.000 description 8
• 229910052783 alkali metal Inorganic materials 0.000 description 8
• 229910052784 alkaline earth metal Inorganic materials 0.000 description 8
• HTFFABIIOAKIBH-UHFFFAOYSA-N diazinane Chemical class C1CCNNC1 HTFFABIIOAKIBH-UHFFFAOYSA-N 0.000 description 8
• 229920002866 paraformaldehyde Polymers 0.000 description 8
• 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 8
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 8
• ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 7
• YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 7
• 230000002378 acidificating effect Effects 0.000 description 7
• 239000013543 active substance Substances 0.000 description 7
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 7
• 239000006185 dispersion Substances 0.000 description 7
• 229910052740 iodine Inorganic materials 0.000 description 7
• 239000011630 iodine Substances 0.000 description 7
• 239000012071 phase Substances 0.000 description 7
• 238000012360 testing method Methods 0.000 description 7
• 238000011282 treatment Methods 0.000 description 7
• QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 6
• OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 6
• ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
• FKNQCJSGGFJEIZ-UHFFFAOYSA-N 4-methylpyridine Chemical compound CC1=CC=NC=C1 FKNQCJSGGFJEIZ-UHFFFAOYSA-N 0.000 description 6
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
• CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 6
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 description 6
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
• IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 6
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 6
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
• OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 6
• ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 6
• NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical class OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 6
• SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 6
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
• 239000007864 aqueous solution Substances 0.000 description 6
• 239000004359 castor oil Substances 0.000 description 6
• 235000019438 castor oil Nutrition 0.000 description 6
• MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 6
• XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 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
• 230000001590 oxidative effect Effects 0.000 description 6
• 239000003444 phase transfer catalyst Substances 0.000 description 6
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
• 238000007363 ring formation reaction Methods 0.000 description 6
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 5
• FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 5
• 241000534944 Thia Species 0.000 description 5
• 239000003377 acid catalyst Substances 0.000 description 5
• 239000012141 concentrate Substances 0.000 description 5
• HCUYBXPSSCRKRF-UHFFFAOYSA-N diphosgene Chemical compound ClC(=O)OC(Cl)(Cl)Cl HCUYBXPSSCRKRF-UHFFFAOYSA-N 0.000 description 5
• 239000000839 emulsion Substances 0.000 description 5
• 229930195733 hydrocarbon Natural products 0.000 description 5
• 150000002430 hydrocarbons Chemical class 0.000 description 5
• KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 5
• 150000002540 isothiocyanates Chemical class 0.000 description 5
• 238000004519 manufacturing process Methods 0.000 description 5
• 238000002844 melting Methods 0.000 description 5
• 230000008018 melting Effects 0.000 description 5
• 150000007530 organic bases Chemical class 0.000 description 5
• 238000002360 preparation method Methods 0.000 description 5
• 239000011541 reaction mixture Substances 0.000 description 5
• 239000000741 silica gel Substances 0.000 description 5
• 229910002027 silica gel Inorganic materials 0.000 description 5
• 238000005507 spraying Methods 0.000 description 5
• SEEPANYCNGTZFQ-UHFFFAOYSA-N sulfadiazine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)NC1=NC=CC=N1 SEEPANYCNGTZFQ-UHFFFAOYSA-N 0.000 description 5
• JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 5
• WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 4
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
• VTIRNZBEJBPYCV-UHFFFAOYSA-N 1-hydrazinylethanol Chemical compound CC(O)NN VTIRNZBEJBPYCV-UHFFFAOYSA-N 0.000 description 4
• QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 4
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 description 4
• UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 4
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
• AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
• JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 4
• IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
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