CH621091A5 - - Google Patents
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- Publication number
- CH621091A5 CH621091A5 CH427976A CH427976A CH621091A5 CH 621091 A5 CH621091 A5 CH 621091A5 CH 427976 A CH427976 A CH 427976A CH 427976 A CH427976 A CH 427976A CH 621091 A5 CH621091 A5 CH 621091A5
- Authority
- CH
- Switzerland
- Prior art keywords
- group
- phenyl
- alkyl
- ethyl
- methyl
- Prior art date
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- -1 1-ethyl-2-methyl-1 H-benz [g] indolyl Chemical group 0.000 claims description 80
- 150000001875 compounds Chemical class 0.000 claims description 33
- 238000002360 preparation method Methods 0.000 claims description 20
- 125000000217 alkyl group Chemical group 0.000 claims description 18
- 238000000034 method Methods 0.000 claims description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
- 239000003593 chromogenic compound Substances 0.000 claims description 10
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 9
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 9
- 239000000463 material Substances 0.000 claims description 9
- HIYWOHBEPVGIQN-UHFFFAOYSA-N 1h-benzo[g]indole Chemical compound C1=CC=CC2=C(NC=C3)C3=CC=C21 HIYWOHBEPVGIQN-UHFFFAOYSA-N 0.000 claims description 7
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 230000008569 process Effects 0.000 claims description 6
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 150000008065 acid anhydrides Chemical class 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 125000000950 dibromo group Chemical group Br* 0.000 claims description 3
- 125000003963 dichloro group Chemical group Cl* 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
- 125000001246 bromo group Chemical group Br* 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 3
- 125000004442 acylamino group Chemical group 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- 239000003337 fertilizer Substances 0.000 claims 1
- 150000004678 hydrides Chemical class 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 18
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- HYCYLTKZFJHVLP-UHFFFAOYSA-N 1-ethyl-2-methylbenzo[g]indole Chemical compound C1=CC=CC2=C3N(CC)C(C)=CC3=CC=C21 HYCYLTKZFJHVLP-UHFFFAOYSA-N 0.000 description 13
- 150000004715 keto acids Chemical class 0.000 description 12
- 229920001568 phenolic resin Polymers 0.000 description 10
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 description 9
- 239000004927 clay Substances 0.000 description 9
- 239000005011 phenolic resin Substances 0.000 description 9
- 239000000126 substance Substances 0.000 description 9
- 150000008064 anhydrides Chemical class 0.000 description 7
- 238000002844 melting Methods 0.000 description 7
- 230000008018 melting Effects 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 239000000758 substrate Substances 0.000 description 6
- 230000002378 acidificating effect Effects 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 4
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 4
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 4
- 125000000814 indol-3-yl group Chemical group [H]C1=C([H])C([H])=C2N([H])C([H])=C([*])C2=C1[H] 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- WTMJHBZSSSDBFQ-UHFFFAOYSA-N 2,3,4-trimethyl-1h-pyrrole Chemical compound CC1=CNC(C)=C1C WTMJHBZSSSDBFQ-UHFFFAOYSA-N 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- AWJWCTOOIBYHON-UHFFFAOYSA-N furo[3,4-b]pyrazine-5,7-dione Chemical compound C1=CN=C2C(=O)OC(=O)C2=N1 AWJWCTOOIBYHON-UHFFFAOYSA-N 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- WNZQDUSMALZDQF-UHFFFAOYSA-N 2-benzofuran-1(3H)-one Chemical compound C1=CC=C2C(=O)OCC2=C1 WNZQDUSMALZDQF-UHFFFAOYSA-N 0.000 description 2
- ALIHHRJMNTXXJT-UHFFFAOYSA-N 2-phenyl-1h-benzo[g]indole Chemical compound N1C(C2=CC=CC=C2C=C2)=C2C=C1C1=CC=CC=C1 ALIHHRJMNTXXJT-UHFFFAOYSA-N 0.000 description 2
- 239000002841 Lewis acid Substances 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 230000018044 dehydration Effects 0.000 description 2
- 238000006297 dehydration reaction Methods 0.000 description 2
- GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 description 2
- MCQOWYALZVKMAR-UHFFFAOYSA-N furo[3,4-b]pyridine-5,7-dione Chemical compound C1=CC=C2C(=O)OC(=O)C2=N1 MCQOWYALZVKMAR-UHFFFAOYSA-N 0.000 description 2
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 2
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- 150000007517 lewis acids Chemical class 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- AUHHYELHRWCWEZ-UHFFFAOYSA-N tetrachlorophthalic anhydride Chemical compound ClC1=C(Cl)C(Cl)=C2C(=O)OC(=O)C2=C1Cl AUHHYELHRWCWEZ-UHFFFAOYSA-N 0.000 description 2
- OXHNLMTVIGZXSG-UHFFFAOYSA-N 1-Methylpyrrole Chemical compound CN1C=CC=C1 OXHNLMTVIGZXSG-UHFFFAOYSA-N 0.000 description 1
- PARCZCNPWOCVSU-UHFFFAOYSA-N 1-hexylbenzo[g]indole Chemical compound C1=CC=CC2=C3N(CCCCCC)C=CC3=CC=C21 PARCZCNPWOCVSU-UHFFFAOYSA-N 0.000 description 1
- GEZGAZKEOUKLBR-UHFFFAOYSA-N 1-phenylpyrrole Chemical compound C1=CC=CN1C1=CC=CC=C1 GEZGAZKEOUKLBR-UHFFFAOYSA-N 0.000 description 1
- WELCYWIRXVLUGM-UHFFFAOYSA-N 2,3,4,5-tetrachloro-6-(1-ethyl-2-methylindole-3-carbonyl)benzoic acid Chemical compound C12=CC=CC=C2N(CC)C(C)=C1C(=O)C1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1C(O)=O WELCYWIRXVLUGM-UHFFFAOYSA-N 0.000 description 1
- JYILHMMEEBFSKH-UHFFFAOYSA-N 2,3,4,5-tetrachloro-6-[4-(diethylamino)benzoyl]benzoic acid Chemical compound C1=CC(N(CC)CC)=CC=C1C(=O)C1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1C(O)=O JYILHMMEEBFSKH-UHFFFAOYSA-N 0.000 description 1
- ZWVBUDPQGPFIRX-UHFFFAOYSA-N 2-(1-ethyl-2-methylindole-3-carbonyl)benzoic acid Chemical compound C12=CC=CC=C2N(CC)C(C)=C1C(=O)C1=CC=CC=C1C(O)=O ZWVBUDPQGPFIRX-UHFFFAOYSA-N 0.000 description 1
- MYKDAIOTKRAMQT-UHFFFAOYSA-N 2-butyl-1-phenylbenzo[g]indole Chemical compound CCCCC1=CC2=CC=C3C=CC=CC3=C2N1C1=CC=CC=C1 MYKDAIOTKRAMQT-UHFFFAOYSA-N 0.000 description 1
- MXTSKGMKOUFSGU-UHFFFAOYSA-N 2-hexyl-1-methylbenzo[g]indole Chemical compound C1=CC=CC2=C(N(C(CCCCCC)=C3)C)C3=CC=C21 MXTSKGMKOUFSGU-UHFFFAOYSA-N 0.000 description 1
- FLUACKUJKJAYKI-UHFFFAOYSA-N 2-methyl-1h-benzo[g]indole Chemical compound C1=CC=CC2=C(NC(C)=C3)C3=CC=C21 FLUACKUJKJAYKI-UHFFFAOYSA-N 0.000 description 1
- KFYCXQJRCZFTTL-UHFFFAOYSA-N 3-(1-ethyl-2-methylbenzo[g]indol-3-yl)-3-(1-ethyl-2-methylindol-3-yl)-2-benzofuran-1-one Chemical compound C1=CC2=CC=CC=C2C2=C1C(C1(C3=CC=CC=C3C(=O)O1)C1=C(C)N(C3=CC=CC=C31)CC)=C(C)N2CC KFYCXQJRCZFTTL-UHFFFAOYSA-N 0.000 description 1
- FMHDTYNGPJYEHT-UHFFFAOYSA-N 3-(1-ethyl-2-methylindole-3-carbonyl)pyrazine-2-carboxylic acid Chemical compound C12=CC=CC=C2N(CC)C(C)=C1C(=O)C1=NC=CN=C1C(O)=O FMHDTYNGPJYEHT-UHFFFAOYSA-N 0.000 description 1
- NFKMAYYHLXEVDM-UHFFFAOYSA-N 3-(1h-indol-3-yl)-3h-2-benzofuran-1-one Chemical class C12=CC=CC=C2C(=O)OC1C1=CNC2=CC=CC=C12 NFKMAYYHLXEVDM-UHFFFAOYSA-N 0.000 description 1
- PYSRRFNXTXNWCD-UHFFFAOYSA-N 3-(2-phenylethenyl)furan-2,5-dione Chemical compound O=C1OC(=O)C(C=CC=2C=CC=CC=2)=C1 PYSRRFNXTXNWCD-UHFFFAOYSA-N 0.000 description 1
- QFRCOKPEGCZUKJ-UHFFFAOYSA-N 4,5,6,7-tetrachloro-3-[4-(diethylamino)phenyl]-3-(1-ethyl-2-methylbenzo[g]indol-3-yl)-2-benzofuran-1-one Chemical compound C1=CC(N(CC)CC)=CC=C1C1(C=2C3=C(C4=CC=CC=C4C=C3)N(CC)C=2C)C(C(Cl)=C(Cl)C(Cl)=C2Cl)=C2C(=O)O1 QFRCOKPEGCZUKJ-UHFFFAOYSA-N 0.000 description 1
- WSKSHHDHKIAMKX-UHFFFAOYSA-N 4,5,6-trichloro-2-benzofuran-1,3-dione Chemical compound ClC1=C(Cl)C(Cl)=CC2=C1C(=O)OC2=O WSKSHHDHKIAMKX-UHFFFAOYSA-N 0.000 description 1
- ROFZMKDROVBLNY-UHFFFAOYSA-N 4-nitro-2-benzofuran-1,3-dione Chemical compound [O-][N+](=O)C1=CC=CC2=C1C(=O)OC2=O ROFZMKDROVBLNY-UHFFFAOYSA-N 0.000 description 1
- FIUAKOPOCYNCCY-UHFFFAOYSA-N 5-(dihexylamino)-2-benzofuran-1,3-dione Chemical compound CCCCCCN(CCCCCC)C1=CC=C2C(=O)OC(=O)C2=C1 FIUAKOPOCYNCCY-UHFFFAOYSA-N 0.000 description 1
- WKOPFKCDGGWLAV-UHFFFAOYSA-N 5-(dimethylamino)-2-benzofuran-1,3-dione Chemical compound CN(C)C1=CC=C2C(=O)OC(=O)C2=C1 WKOPFKCDGGWLAV-UHFFFAOYSA-N 0.000 description 1
- MMVIDXVHQANYAE-UHFFFAOYSA-N 5-nitro-2-benzofuran-1,3-dione Chemical compound [O-][N+](=O)C1=CC=C2C(=O)OC(=O)C2=C1 MMVIDXVHQANYAE-UHFFFAOYSA-N 0.000 description 1
- OYLUOPBYVMUUBF-UHFFFAOYSA-N 6-methyl-4-propyl-2-benzofuran-1,3-dione Chemical compound CCCC1=CC(C)=CC2=C1C(=O)OC2=O OYLUOPBYVMUUBF-UHFFFAOYSA-N 0.000 description 1
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical group OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 1
- 229930194542 Keto Natural products 0.000 description 1
- 206010024769 Local reaction Diseases 0.000 description 1
- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 229920000147 Styrene maleic anhydride Polymers 0.000 description 1
- QHWKHLYUUZGSCW-UHFFFAOYSA-N Tetrabromophthalic anhydride Chemical compound BrC1=C(Br)C(Br)=C2C(=O)OC(=O)C2=C1Br QHWKHLYUUZGSCW-UHFFFAOYSA-N 0.000 description 1
- 229910021536 Zeolite Inorganic materials 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 125000003282 alkyl amino group Chemical group 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- HPTYUNKZVDYXLP-UHFFFAOYSA-N aluminum;trihydroxy(trihydroxysilyloxy)silane;hydrate Chemical compound O.[Al].[Al].O[Si](O)(O)O[Si](O)(O)O HPTYUNKZVDYXLP-UHFFFAOYSA-N 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 229960000892 attapulgite Drugs 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 229940096529 carboxypolymethylene Drugs 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- LQEJKDNALLXRCT-UHFFFAOYSA-N chloroform;toluene Chemical compound ClC(Cl)Cl.CC1=CC=CC=C1 LQEJKDNALLXRCT-UHFFFAOYSA-N 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 230000009089 cytolysis Effects 0.000 description 1
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 1
- SLGWESQGEUXWJQ-UHFFFAOYSA-N formaldehyde;phenol Chemical compound O=C.OC1=CC=CC=C1 SLGWESQGEUXWJQ-UHFFFAOYSA-N 0.000 description 1
- 230000008570 general process Effects 0.000 description 1
- 229910052621 halloysite Inorganic materials 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 125000000686 lactone group Chemical group 0.000 description 1
- 230000031700 light absorption Effects 0.000 description 1
- 239000006193 liquid solution Substances 0.000 description 1
- 230000005577 local transmission Effects 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- CWOMTHDOJCARBY-UHFFFAOYSA-N n,n,3-trimethylaniline Chemical compound CN(C)C1=CC=CC(C)=C1 CWOMTHDOJCARBY-UHFFFAOYSA-N 0.000 description 1
- 229910052625 palygorskite Inorganic materials 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 125000005506 phthalide group Chemical class 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/87—Benzo [c] furans; Hydrogenated benzo [c] furans
- C07D307/89—Benzo [c] furans; Hydrogenated benzo [c] furans with two oxygen atoms directly attached in positions 1 and 3
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Color Printing (AREA)
- Heat Sensitive Colour Forming Recording (AREA)
- Indole Compounds (AREA)
- Photoreceptors In Electrophotography (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/566,854 US4016174A (en) | 1975-04-10 | 1975-04-10 | Benzoindole phthalides |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH621091A5 true CH621091A5 (es) | 1981-01-15 |
Family
ID=24264671
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH427976A CH621091A5 (es) | 1975-04-10 | 1976-04-06 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US4016174A (es) |
| JP (4) | JPS5827824B2 (es) |
| CA (1) | CA1055943A (es) |
| CH (1) | CH621091A5 (es) |
| DE (1) | DE2615035A1 (es) |
| FR (1) | FR2306989A1 (es) |
| GB (1) | GB1499077A (es) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4189171A (en) * | 1977-03-01 | 1980-02-19 | Sterling Drug Inc. | Marking systems containing 3-aryl-3-heterylphthalides and 3,3-bis(heteryl)phthalides |
| US4275206A (en) * | 1979-03-05 | 1981-06-23 | Appleton Papers Inc. | Lactone compounds containing an indolizine radical |
| GB2194070B (en) * | 1986-07-09 | 1990-01-10 | Fuji Photo Film Co Ltd | Sheet recording material containing dye-forming components |
| US5041547A (en) * | 1986-08-28 | 1991-08-20 | Appleton Papers Inc. | Chromogenic substituted 4,7-diazaphthalides |
| US4996328A (en) * | 1989-03-08 | 1991-02-26 | Appleton Papers Inc. | Bis-(indolyl)ethylenes |
| US5116978A (en) * | 1989-03-08 | 1992-05-26 | Appleton Papers Inc. | Process for bis(indolyl)ethylene synthesis |
| US5039821A (en) * | 1989-08-23 | 1991-08-13 | Appleton Papers Inc. | Process for producing di[bis-(indolyl)ethylenyl]tetrahalophthalides |
| JP3271226B2 (ja) * | 1994-01-25 | 2002-04-02 | 山本化成株式会社 | フタリド化合物、およびこれを用いる近赤外線吸収剤並びに記録材料 |
| EP1700907A1 (en) | 2005-03-11 | 2006-09-13 | Unilever N.V. | Liquid bleaching composition |
| EP3964633A1 (en) | 2020-09-04 | 2022-03-09 | LG Electronics Inc. | Laundry treating apparatus |
| US20220074110A1 (en) | 2020-09-04 | 2022-03-10 | Lg Electronics Inc. | Laundry treating apparatus |
| CN116324078A (zh) | 2020-10-05 | 2023-06-23 | Lg电子株式会社 | 衣物处理装置 |
| EP4039872A3 (en) | 2021-02-08 | 2022-11-02 | LG Electronics Inc. | Laundry treating apparatus and method for controlling the same |
| KR20220114275A (ko) | 2021-02-08 | 2022-08-17 | 엘지전자 주식회사 | 의류처리장치 |
| KR20220114284A (ko) | 2021-02-08 | 2022-08-17 | 엘지전자 주식회사 | 의류처리장치 |
| KR20220114270A (ko) | 2021-02-08 | 2022-08-17 | 엘지전자 주식회사 | 의류처리장치 |
| KR20220114268A (ko) | 2021-02-08 | 2022-08-17 | 엘지전자 주식회사 | 의류처리장치 |
| CN114941223A (zh) | 2021-02-08 | 2022-08-26 | Lg电子株式会社 | 衣物处理装置 |
| KR20230124653A (ko) | 2021-02-08 | 2023-08-25 | 엘지전자 주식회사 | 의류처리장치 |
| KR20220114269A (ko) | 2021-02-08 | 2022-08-17 | 엘지전자 주식회사 | 의류처리장치 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3736337A (en) * | 1971-04-27 | 1973-05-29 | Ncr Co | Tetrahalogenated chromogenic compounds and their use |
-
1975
- 1975-04-10 US US05/566,854 patent/US4016174A/en not_active Expired - Lifetime
- 1975-11-04 CA CA238,992A patent/CA1055943A/en not_active Expired
-
1976
- 1976-01-20 JP JP51005387A patent/JPS5827824B2/ja not_active Expired
- 1976-03-15 GB GB10210/76A patent/GB1499077A/en not_active Expired
- 1976-04-06 CH CH427976A patent/CH621091A5/de not_active IP Right Cessation
- 1976-04-07 DE DE19762615035 patent/DE2615035A1/de not_active Ceased
- 1976-04-09 FR FR7610424A patent/FR2306989A1/fr active Granted
-
1980
- 1980-02-12 JP JP1589380A patent/JPS55115455A/ja active Pending
- 1980-02-12 JP JP1589280A patent/JPS55115454A/ja active Pending
- 1980-02-12 JP JP55015891A patent/JPS609535B2/ja not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| JPS55115455A (en) | 1980-09-05 |
| JPS5827824B2 (ja) | 1983-06-11 |
| CA1055943A (en) | 1979-06-05 |
| FR2306989A1 (fr) | 1976-11-05 |
| JPS51121036A (en) | 1976-10-22 |
| JPS55115453A (en) | 1980-09-05 |
| JPS55115454A (en) | 1980-09-05 |
| FR2306989B1 (es) | 1980-01-04 |
| GB1499077A (en) | 1978-01-25 |
| US4016174A (en) | 1977-04-05 |
| JPS609535B2 (ja) | 1985-03-11 |
| DE2615035A1 (de) | 1976-11-04 |
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| Date | Code | Title | Description |
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| PL | Patent ceased |