CA2093611A1

CA2093611A1 - Fluorine-free titanocenes and the use thereof

Fluorine-free titanocenes and the use thereof

Info

Publication number: CA2093611A1
Authority: CA; Canada
Prior art keywords: substituted; unsubstituted; phenyl; c4alkyl; radicals
Prior art date: 1992-04-09
Legal status : Abandoned

Application number

CA002093611A

Other languages

English (en)

French (fr)

Inventor

Vincent Desobry

Current Assignee

BASF Schweiz AG

Original Assignee

Ciba Geigy AG

Priority date

1992-04-09

Filing date

1993-04-07

Publication date

1993-10-10

1993-04-07 Application filed by Ciba Geigy AG filed Critical Ciba Geigy AG

1993-10-10 Publication of CA2093611A1 publication Critical patent/CA2093611A1/en

Status Abandoned legal-status Critical Current

Links

-1 biphenylyl Chemical group 0.000 claims abstract description 210
150000001875 compounds Chemical class 0.000 claims abstract description 189
239000000460 chlorine Substances 0.000 claims abstract description 163
229910052757 nitrogen Inorganic materials 0.000 claims abstract description 120
229910052801 chlorine Inorganic materials 0.000 claims abstract description 110
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 70
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 66
229910052794 bromium Inorganic materials 0.000 claims abstract description 51
229910052740 iodine Inorganic materials 0.000 claims abstract description 35
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 33
125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 20
239000001257 hydrogen Substances 0.000 claims abstract description 17
125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 17
ZSWFCLXCOIISFI-UHFFFAOYSA-N endo-cyclopentadiene Natural products C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 claims abstract description 15
125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims abstract description 14
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 12
125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 claims abstract description 11
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims abstract description 9
229910052760 oxygen Inorganic materials 0.000 claims abstract description 9
239000005977 Ethylene Substances 0.000 claims abstract description 8
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 8
239000001301 oxygen Substances 0.000 claims abstract description 8
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims abstract description 7
125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims abstract description 6
125000004434 sulfur atom Chemical group 0.000 claims abstract description 6
CPEONABTMRSIKA-UHFFFAOYSA-N 1,4$l^{2}-oxazinane Chemical compound C1COCC[N]1 CPEONABTMRSIKA-UHFFFAOYSA-N 0.000 claims abstract description 5
125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims abstract 8
125000002373 5 membered heterocyclic group Chemical group 0.000 claims abstract 3
125000004070 6 membered heterocyclic group Chemical group 0.000 claims abstract 3
239000000203 mixture Substances 0.000 claims description 87
238000000034 method Methods 0.000 claims description 42
239000002904 solvent Substances 0.000 claims description 27
125000004430 oxygen atom Chemical group O* 0.000 claims description 21
125000000951 phenoxy group Chemical class [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 19
239000000463 material Substances 0.000 claims description 17
125000001624 naphthyl group Chemical group 0.000 claims description 15
229920000642 polymer Polymers 0.000 claims description 14
239000000758 substrate Substances 0.000 claims description 14
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 13
125000001544 thienyl group Chemical group 0.000 claims description 12
125000003320 C2-C6 alkenyloxy group Chemical class 0.000 claims description 11
238000004519 manufacturing process Methods 0.000 claims description 11
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 10
125000002541 furyl group Chemical group 0.000 claims description 10
125000002883 imidazolyl group Chemical group 0.000 claims description 10
238000007639 printing Methods 0.000 claims description 10
125000004076 pyridyl group Chemical group 0.000 claims description 10
125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 claims description 8
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 8
125000005561 phenanthryl group Chemical group 0.000 claims description 8
239000000654 additive Substances 0.000 claims description 7
239000003973 paint Substances 0.000 claims description 7
125000006710 (C2-C12) alkenyl group Chemical group 0.000 claims description 5
125000004093 cyano group Chemical group *C#N 0.000 claims description 5
239000000976 ink Substances 0.000 claims description 5
125000000714 pyrimidinyl group Chemical group 0.000 claims description 5
125000006552 (C3-C8) cycloalkyl group Chemical class 0.000 claims description 4
125000000051 benzyloxy group Chemical class [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 4
125000004642 (C1-C12) alkoxy group Chemical class 0.000 claims 9
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 2
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 2
YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims 2
125000006374 C2-C10 alkenyl group Chemical group 0.000 claims 2
125000004648 C2-C8 alkenyl group Chemical group 0.000 claims 2
125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims 2
125000000217 alkyl group Chemical group 0.000 abstract description 12
125000003545 alkoxy group Chemical group 0.000 abstract description 4
125000003342 alkenyl group Chemical group 0.000 abstract description 3
125000000753 cycloalkyl group Chemical group 0.000 abstract 3
125000004414 alkyl thio group Chemical group 0.000 abstract 2
125000000000 cycloalkoxy group Chemical group 0.000 abstract 2
125000003302 alkenyloxy group Chemical group 0.000 abstract 1
125000005366 cycloalkylthio group Chemical group 0.000 abstract 1
KOMDZQSPRDYARS-UHFFFAOYSA-N cyclopenta-1,3-diene titanium Chemical class [Ti].C1C=CC=C1.C1C=CC=C1 KOMDZQSPRDYARS-UHFFFAOYSA-N 0.000 abstract 1
238000002360 preparation method Methods 0.000 description 64
238000000921 elemental analysis Methods 0.000 description 61
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 42
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 42
150000003254 radicals Chemical class 0.000 description 42
229910001868 water Inorganic materials 0.000 description 39
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 38
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
239000000047 product Substances 0.000 description 36
238000002844 melting Methods 0.000 description 35
230000008018 melting Effects 0.000 description 35
239000000243 solution Substances 0.000 description 35
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 33
CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 29
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 27
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 26
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 26
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 26
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 25
239000010410 layer Substances 0.000 description 25
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 24
229910052943 magnesium sulfate Inorganic materials 0.000 description 21
235000019341 magnesium sulphate Nutrition 0.000 description 21
239000000725 suspension Substances 0.000 description 21
239000012074 organic phase Substances 0.000 description 20
125000004429 atom Chemical group 0.000 description 18
229910052717 sulfur Inorganic materials 0.000 description 18
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 17
229920001577 copolymer Polymers 0.000 description 17
239000011541 reaction mixture Substances 0.000 description 17
238000012360 testing method Methods 0.000 description 17
238000006243 chemical reaction Methods 0.000 description 16
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
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 15
239000007789 gas Substances 0.000 description 14
229910052786 argon Inorganic materials 0.000 description 13
PESYEWKSBIWTAK-UHFFFAOYSA-N cyclopenta-1,3-diene;titanium(2+) Chemical class [Ti+2].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 PESYEWKSBIWTAK-UHFFFAOYSA-N 0.000 description 13
229910052751 metal Inorganic materials 0.000 description 13
239000002184 metal Substances 0.000 description 13
229920005989 resin Polymers 0.000 description 13
239000011347 resin Substances 0.000 description 13
YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 12
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 12
238000000576 coating method Methods 0.000 description 12
239000007787 solid Substances 0.000 description 12
239000003480 eluent Substances 0.000 description 11
229940093499 ethyl acetate Drugs 0.000 description 11
235000019439 ethyl acetate Nutrition 0.000 description 11
239000007788 liquid Substances 0.000 description 11
239000000178 monomer Substances 0.000 description 11
229920005862 polyol Polymers 0.000 description 11
239000000377 silicon dioxide Substances 0.000 description 11
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical group [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 10
150000001252 acrylic acid derivatives Chemical class 0.000 description 10
229910052681 coesite Inorganic materials 0.000 description 10
229910052906 cristobalite Inorganic materials 0.000 description 10
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
PHTQWCKDNZKARW-UHFFFAOYSA-N isoamylol Chemical compound CC(C)CCO PHTQWCKDNZKARW-UHFFFAOYSA-N 0.000 description 10
235000012239 silicon dioxide Nutrition 0.000 description 10
229910052682 stishovite Inorganic materials 0.000 description 10
229910052905 tridymite Inorganic materials 0.000 description 10
238000001035 drying Methods 0.000 description 9
150000003077 polyols Chemical class 0.000 description 9
150000003230 pyrimidines Chemical class 0.000 description 9
TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 8
IWTBVKIGCDZRPL-LURJTMIESA-N 3-Methylbutanol Natural products CC[C@H](C)CCO IWTBVKIGCDZRPL-LURJTMIESA-N 0.000 description 8
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 8
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 8
239000012298 atmosphere Substances 0.000 description 8
239000002585 base Substances 0.000 description 8
125000004432 carbon atom Chemical group C* 0.000 description 8
239000003999 initiator Substances 0.000 description 8
229910052708 sodium Inorganic materials 0.000 description 8
239000011734 sodium Substances 0.000 description 8
RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical group [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 7
239000003795 chemical substances by application Substances 0.000 description 7
125000000623 heterocyclic group Chemical group 0.000 description 7
125000001424 substituent group Chemical group 0.000 description 7
238000006277 sulfonation reaction Methods 0.000 description 7
229910052719 titanium Inorganic materials 0.000 description 7
FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 6
FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 6
NRFQZTCQAYEXEE-UHFFFAOYSA-N Fenclorim Chemical compound ClC1=CC(Cl)=NC(C=2C=CC=CC=2)=N1 NRFQZTCQAYEXEE-UHFFFAOYSA-N 0.000 description 6
JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 6
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
239000007983 Tris buffer Substances 0.000 description 6
125000003118 aryl group Chemical group 0.000 description 6
239000011248 coating agent Substances 0.000 description 6
239000006185 dispersion Substances 0.000 description 6
238000003818 flash chromatography Methods 0.000 description 6
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 6
230000003287 optical effect Effects 0.000 description 6
229920002120 photoresistant polymer Polymers 0.000 description 6
229920000728 polyester Polymers 0.000 description 6
229920006267 polyester film Polymers 0.000 description 6
230000001681 protective effect Effects 0.000 description 6
239000000600 sorbitol Substances 0.000 description 6
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 6
239000010936 titanium Substances 0.000 description 6
OEHNQSUFMAPKMU-UHFFFAOYSA-N 3,5-dichloro-1-phenylpyrazole Chemical compound N1=C(Cl)C=C(Cl)N1C1=CC=CC=C1 OEHNQSUFMAPKMU-UHFFFAOYSA-N 0.000 description 5
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 5
WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 5
HVVWZTWDBSEWIH-UHFFFAOYSA-N [2-(hydroxymethyl)-3-prop-2-enoyloxy-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(CO)(COC(=O)C=C)COC(=O)C=C HVVWZTWDBSEWIH-UHFFFAOYSA-N 0.000 description 5
150000001412 amines Chemical class 0.000 description 5
238000004458 analytical method Methods 0.000 description 5
239000011230 binding agent Substances 0.000 description 5
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 5
125000001309 chloro group Chemical group Cl* 0.000 description 5
150000002009 diols Chemical class 0.000 description 5
150000002148 esters Chemical group 0.000 description 5
229910052731 fluorine Inorganic materials 0.000 description 5
239000011737 fluorine Substances 0.000 description 5
239000003960 organic solvent Substances 0.000 description 5
229920000647 polyepoxide Polymers 0.000 description 5
229920002635 polyurethane Polymers 0.000 description 5
239000004814 polyurethane Substances 0.000 description 5
239000002244 precipitate Substances 0.000 description 5
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
230000035945 sensitivity Effects 0.000 description 5
239000007858 starting material Substances 0.000 description 5
239000000126 substance Substances 0.000 description 5
KUDUQBURMYMBIJ-UHFFFAOYSA-N 2-prop-2-enoyloxyethyl prop-2-enoate Chemical compound C=CC(=O)OCCOC(=O)C=C KUDUQBURMYMBIJ-UHFFFAOYSA-N 0.000 description 4
JOOXCMJARBKPKM-UHFFFAOYSA-N 4-oxopentanoic acid Chemical compound CC(=O)CCC(O)=O JOOXCMJARBKPKM-UHFFFAOYSA-N 0.000 description 4
101150041968 CDC13 gene Proteins 0.000 description 4
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 4
QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 4
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
239000004952 Polyamide Substances 0.000 description 4
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 4
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
239000005030 aluminium foil Substances 0.000 description 4
239000008346 aqueous phase Substances 0.000 description 4
239000012965 benzophenone Substances 0.000 description 4
239000004305 biphenyl Substances 0.000 description 4
235000010290 biphenyl Nutrition 0.000 description 4
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
150000001735 carboxylic acids Chemical class 0.000 description 4
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
239000000975 dye Substances 0.000 description 4
229910052736 halogen Inorganic materials 0.000 description 4
150000002367 halogens Chemical class 0.000 description 4
125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
239000005457 ice water Substances 0.000 description 4
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 4
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 4
239000011976 maleic acid Substances 0.000 description 4
150000002734 metacrylic acid derivatives Chemical class 0.000 description 4
239000000123 paper Substances 0.000 description 4
ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
229920002647 polyamide Polymers 0.000 description 4
229920000036 polyvinylpyrrolidone Polymers 0.000 description 4
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 4
229910000104 sodium hydride Inorganic materials 0.000 description 4
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
238000004809 thin layer chromatography Methods 0.000 description 4
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 4
238000002604 ultrasonography Methods 0.000 description 4
GIKMWFAAEIACRF-UHFFFAOYSA-N 2,4,5-trichloropyrimidine Chemical compound ClC1=NC=C(Cl)C(Cl)=N1 GIKMWFAAEIACRF-UHFFFAOYSA-N 0.000 description 3
DPVIABCMTHHTGB-UHFFFAOYSA-N 2,4,6-trichloropyrimidine Chemical compound ClC1=CC(Cl)=NC(Cl)=N1 DPVIABCMTHHTGB-UHFFFAOYSA-N 0.000 description 3
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
MSXVEPNJUHWQHW-UHFFFAOYSA-N 2-methylbutan-2-ol Chemical compound CCC(C)(C)O MSXVEPNJUHWQHW-UHFFFAOYSA-N 0.000 description 3
GJNGXPDXRVXSEH-UHFFFAOYSA-N 4-chlorobenzonitrile Chemical compound ClC1=CC=C(C#N)C=C1 GJNGXPDXRVXSEH-UHFFFAOYSA-N 0.000 description 3
LQLQRFGHAALLLE-UHFFFAOYSA-N 5-bromouracil Chemical compound BrC1=CNC(=O)NC1=O LQLQRFGHAALLLE-UHFFFAOYSA-N 0.000 description 3
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 3
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 3
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 3
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