CH621545A5 - - Google Patents
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- Publication number
- CH621545A5 CH621545A5 CH652176A CH652176A CH621545A5 CH 621545 A5 CH621545 A5 CH 621545A5 CH 652176 A CH652176 A CH 652176A CH 652176 A CH652176 A CH 652176A CH 621545 A5 CH621545 A5 CH 621545A5
- Authority
- CH
- Switzerland
- Prior art keywords
- formula
- alkyl
- carbon atoms
- hydrogen
- quinoxalines
- Prior art date
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 36
- 150000003252 quinoxalines Chemical class 0.000 claims description 35
- 125000004432 carbon atom Chemical group C* 0.000 claims description 33
- 125000000217 alkyl group Chemical group 0.000 claims description 32
- -1 alkyl radical Chemical class 0.000 claims description 32
- 239000001257 hydrogen Substances 0.000 claims description 31
- 229910052739 hydrogen Inorganic materials 0.000 claims description 31
- 238000004061 bleaching Methods 0.000 claims description 30
- 238000000034 method Methods 0.000 claims description 20
- 239000003054 catalyst Substances 0.000 claims description 18
- 229910052709 silver Inorganic materials 0.000 claims description 17
- 239000004332 silver Substances 0.000 claims description 17
- 238000002360 preparation method Methods 0.000 claims description 16
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 15
- 239000002904 solvent Substances 0.000 claims description 14
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 claims description 13
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 13
- 125000003118 aryl group Chemical group 0.000 claims description 12
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 10
- 150000002431 hydrogen Chemical class 0.000 claims description 9
- QSJXEFYPDANLFS-UHFFFAOYSA-N Diacetyl Chemical group CC(=O)C(C)=O QSJXEFYPDANLFS-UHFFFAOYSA-N 0.000 claims description 7
- 229910052783 alkali metal Inorganic materials 0.000 claims description 6
- 238000009833 condensation Methods 0.000 claims description 6
- 230000005494 condensation Effects 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 150000004984 aromatic diamines Chemical class 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- NFGODEMQGQNUKK-UHFFFAOYSA-M [6-(diethylamino)-9-(2-octadecoxycarbonylphenyl)xanthen-3-ylidene]-diethylazanium;chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCCCOC(=O)C1=CC=CC=C1C1=C2C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C21 NFGODEMQGQNUKK-UHFFFAOYSA-M 0.000 claims description 3
- 125000003107 substituted aryl group Chemical group 0.000 claims description 3
- 150000004982 aromatic amines Chemical class 0.000 claims 2
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 27
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 25
- 150000001875 compounds Chemical class 0.000 description 25
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- 239000000243 solution Substances 0.000 description 20
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
- 229910001868 water Inorganic materials 0.000 description 16
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- 239000010410 layer Substances 0.000 description 13
- 150000003254 radicals Chemical class 0.000 description 13
- 239000011734 sodium Substances 0.000 description 13
- 239000000047 product Substances 0.000 description 12
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 11
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 11
- 239000000203 mixture Substances 0.000 description 11
- 229910052700 potassium Inorganic materials 0.000 description 11
- 239000011591 potassium Substances 0.000 description 11
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 10
- WFDIJRYMOXRFFG-UHFFFAOYSA-N acetic acid anhydride Natural products CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 10
- 239000000975 dye Substances 0.000 description 10
- 229910052708 sodium Inorganic materials 0.000 description 10
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 9
- 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
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 8
- 238000002329 infrared spectrum Methods 0.000 description 8
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 8
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Inorganic materials [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 8
- 238000002844 melting Methods 0.000 description 7
- 230000008018 melting Effects 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 239000002879 Lewis base Substances 0.000 description 6
- 229960000583 acetic acid Drugs 0.000 description 6
- 239000000839 emulsion Substances 0.000 description 6
- 150000007527 lewis bases Chemical class 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
- 239000007844 bleaching agent Substances 0.000 description 5
- 238000004587 chromatography analysis Methods 0.000 description 5
- 150000004985 diamines Chemical class 0.000 description 5
- 238000002955 isolation Methods 0.000 description 5
- 125000001424 substituent group Chemical group 0.000 description 5
- 150000005183 1,2-dinitrobenzenes Chemical class 0.000 description 4
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- AEMRFAOFKBGASW-UHFFFAOYSA-M Glycolate Chemical compound OCC([O-])=O AEMRFAOFKBGASW-UHFFFAOYSA-M 0.000 description 4
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 150000003863 ammonium salts Chemical class 0.000 description 4
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- 238000004140 cleaning Methods 0.000 description 4
- 125000005594 diketone group Chemical group 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 239000012362 glacial acetic acid Substances 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- FSSPGSAQUIYDCN-UHFFFAOYSA-N 1,3-Propane sultone Chemical compound O=S1(=O)CCCO1 FSSPGSAQUIYDCN-UHFFFAOYSA-N 0.000 description 3
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2,2'-azo-bis-isobutyronitrile Substances N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 3
- WPEXIPNDKDKUGH-UHFFFAOYSA-N 2,3-dimethylquinoxalin-6-ol Chemical compound C1=C(O)C=C2N=C(C)C(C)=NC2=C1 WPEXIPNDKDKUGH-UHFFFAOYSA-N 0.000 description 3
- UEUIKXVPXLWUDU-UHFFFAOYSA-N 4-diazoniobenzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=C([N+]#N)C=C1 UEUIKXVPXLWUDU-UHFFFAOYSA-N 0.000 description 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 3
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 3
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 3
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 230000002152 alkylating effect Effects 0.000 description 3
- 230000029936 alkylation Effects 0.000 description 3
- 238000005804 alkylation reaction Methods 0.000 description 3
- 239000000987 azo dye Substances 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 238000005266 casting Methods 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- PJUIMOJAAPLTRJ-UHFFFAOYSA-N monothioglycerol Chemical compound OCC(O)CS PJUIMOJAAPLTRJ-UHFFFAOYSA-N 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000007800 oxidant agent Substances 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 235000009518 sodium iodide Nutrition 0.000 description 3
- 159000000000 sodium salts Chemical class 0.000 description 3
- 235000019345 sodium thiosulphate Nutrition 0.000 description 3
- 238000006277 sulfonation reaction Methods 0.000 description 3
- POCJOGNVFHPZNS-ZJUUUORDSA-N (6S,7R)-2-azaspiro[5.5]undecan-7-ol Chemical compound O[C@@H]1CCCC[C@]11CNCCC1 POCJOGNVFHPZNS-ZJUUUORDSA-N 0.000 description 2
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical class NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 2
- ZUFXYUWDSJPBEF-UHFFFAOYSA-N 2,3,7-trimethylquinoxalin-6-amine Chemical compound CC1=C(C)N=C2C=C(N)C(C)=CC2=N1 ZUFXYUWDSJPBEF-UHFFFAOYSA-N 0.000 description 2
- ISELKPUCMKDVFW-UHFFFAOYSA-N 2,3-dimethyl-6-(2-phenoxyethoxy)quinoxaline Chemical compound C1=C2N=C(C)C(C)=NC2=CC=C1OCCOC1=CC=CC=C1 ISELKPUCMKDVFW-UHFFFAOYSA-N 0.000 description 2
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 2
- 229940093475 2-ethoxyethanol Drugs 0.000 description 2
- XWAAVZHMWRDBIP-UHFFFAOYSA-N 2-nitro-4-(2-phenoxyethoxy)aniline Chemical compound C1=C([N+]([O-])=O)C(N)=CC=C1OCCOC1=CC=CC=C1 XWAAVZHMWRDBIP-UHFFFAOYSA-N 0.000 description 2
- DPJCXCZTLWNFOH-UHFFFAOYSA-N 2-nitroaniline Chemical compound NC1=CC=CC=C1[N+]([O-])=O DPJCXCZTLWNFOH-UHFFFAOYSA-N 0.000 description 2
- CWLKGDAVCFYWJK-UHFFFAOYSA-N 3-aminophenol Chemical class NC1=CC=CC(O)=C1 CWLKGDAVCFYWJK-UHFFFAOYSA-N 0.000 description 2
- BMTAFVWTTFSTOG-UHFFFAOYSA-N Butylate Chemical compound CCSC(=O)N(CC(C)C)CC(C)C BMTAFVWTTFSTOG-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- 108010010803 Gelatin Proteins 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 2
- BSPUVYFGURDFHE-UHFFFAOYSA-N Nitramine Natural products CC1C(O)CCC2CCCNC12 BSPUVYFGURDFHE-UHFFFAOYSA-N 0.000 description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
- NPYPAHLBTDXSSS-UHFFFAOYSA-N Potassium ion Chemical compound [K+] NPYPAHLBTDXSSS-UHFFFAOYSA-N 0.000 description 2
- TUCNEACPLKLKNU-UHFFFAOYSA-N acetyl Chemical compound C[C]=O TUCNEACPLKLKNU-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 230000010933 acylation Effects 0.000 description 2
- 238000005917 acylation reaction Methods 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 description 2
- WDIHJSXYQDMJHN-UHFFFAOYSA-L barium chloride Chemical compound [Cl-].[Cl-].[Ba+2] WDIHJSXYQDMJHN-UHFFFAOYSA-L 0.000 description 2
- 229910001626 barium chloride Inorganic materials 0.000 description 2
- 159000000009 barium salts Chemical class 0.000 description 2
- 230000031709 bromination Effects 0.000 description 2
- 238000005893 bromination reaction Methods 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 150000001805 chlorine compounds Chemical class 0.000 description 2
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 229920000159 gelatin Polymers 0.000 description 2
- 239000008273 gelatin Substances 0.000 description 2
- 235000019322 gelatine Nutrition 0.000 description 2
- 235000011852 gelatine desserts Nutrition 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- POCJOGNVFHPZNS-UHFFFAOYSA-N isonitramine Natural products OC1CCCCC11CNCCC1 POCJOGNVFHPZNS-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 229910017604 nitric acid Inorganic materials 0.000 description 2
- 238000010534 nucleophilic substitution reaction Methods 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 2
- FYRHIOVKTDQVFC-UHFFFAOYSA-M potassium phthalimide Chemical compound [K+].C1=CC=C2C(=O)[N-]C(=O)C2=C1 FYRHIOVKTDQVFC-UHFFFAOYSA-M 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- YOWAEZWWQFSEJD-UHFFFAOYSA-N quinoxalin-2-amine Chemical class C1=CC=CC2=NC(N)=CN=C21 YOWAEZWWQFSEJD-UHFFFAOYSA-N 0.000 description 2
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 2
- 239000002356 single layer Substances 0.000 description 2
- 235000017281 sodium acetate Nutrition 0.000 description 2
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000000859 sublimation Methods 0.000 description 2
- 230000008022 sublimation Effects 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- DFKXBDKOBBCUIA-UHFFFAOYSA-N (2,3-dimethylquinoxalin-6-yl)methanol Chemical compound C1=C(CO)C=C2N=C(C)C(C)=NC2=C1 DFKXBDKOBBCUIA-UHFFFAOYSA-N 0.000 description 1
- HMVJXTUUQJUYJI-UHFFFAOYSA-N (3,4-diaminophenyl)methanol Chemical compound NC1=CC=C(CO)C=C1N HMVJXTUUQJUYJI-UHFFFAOYSA-N 0.000 description 1
- GOZRLRVORGAHLI-UHFFFAOYSA-N 1,2-dinitro-4-(2-phenoxyethoxy)benzene Chemical compound C1=C([N+]([O-])=O)C([N+](=O)[O-])=CC=C1OCCOC1=CC=CC=C1 GOZRLRVORGAHLI-UHFFFAOYSA-N 0.000 description 1
- AOSFMYBATFLTAQ-UHFFFAOYSA-N 1-amino-3-(benzimidazol-1-yl)propan-2-ol Chemical compound C1=CC=C2N(CC(O)CN)C=NC2=C1 AOSFMYBATFLTAQ-UHFFFAOYSA-N 0.000 description 1
- HUKXSKKZEXMRTM-UHFFFAOYSA-N 1-methoxy-2-methyl-4,5-dinitrobenzene Chemical compound COC1=CC([N+]([O-])=O)=C([N+]([O-])=O)C=C1C HUKXSKKZEXMRTM-UHFFFAOYSA-N 0.000 description 1
- AWBOSXFRPFZLOP-UHFFFAOYSA-N 2,1,3-benzoxadiazole Chemical class C1=CC=CC2=NON=C21 AWBOSXFRPFZLOP-UHFFFAOYSA-N 0.000 description 1
- GQRWKGBOBWHKHP-UHFFFAOYSA-N 2,3,6-trimethylquinoxaline Chemical compound N1=C(C)C(C)=NC2=CC(C)=CC=C21 GQRWKGBOBWHKHP-UHFFFAOYSA-N 0.000 description 1
- ZSAFSOKZRQIORD-UHFFFAOYSA-N 2,3,7-trimethylquinoxalin-6-ol Chemical compound CC1=C(C)N=C2C=C(O)C(C)=CC2=N1 ZSAFSOKZRQIORD-UHFFFAOYSA-N 0.000 description 1
- VOZKAJLKRJDJLL-UHFFFAOYSA-N 2,4-diaminotoluene Chemical compound CC1=CC=C(N)C=C1N VOZKAJLKRJDJLL-UHFFFAOYSA-N 0.000 description 1
- NFFGWRVCDQKQNN-UHFFFAOYSA-N 2-(2,3-dimethylquinoxalin-6-yl)oxyethanol Chemical compound C1=C(OCCO)C=C2N=C(C)C(C)=NC2=C1 NFFGWRVCDQKQNN-UHFFFAOYSA-N 0.000 description 1
- HBHPUDDHINMUPI-UHFFFAOYSA-N 2-(2-methyl-4,5-dinitrophenoxy)ethanesulfonic acid Chemical compound CC1=CC([N+]([O-])=O)=C([N+]([O-])=O)C=C1OCCS(O)(=O)=O HBHPUDDHINMUPI-UHFFFAOYSA-N 0.000 description 1
- XFFVOZSTRQSSTK-UHFFFAOYSA-N 2-(3,4-diaminophenoxy)ethanesulfonic acid Chemical compound NC1=CC=C(OCCS(O)(=O)=O)C=C1N XFFVOZSTRQSSTK-UHFFFAOYSA-N 0.000 description 1
- CJGGCRWDLMFQSL-UHFFFAOYSA-N 2-(3,4-dinitrophenoxy)ethanesulfonic acid Chemical compound OS(=O)(=O)CCOC1=CC=C([N+]([O-])=O)C([N+]([O-])=O)=C1 CJGGCRWDLMFQSL-UHFFFAOYSA-N 0.000 description 1
- FKHUZRDQJTZMFB-UHFFFAOYSA-N 2-(4,5-diamino-2-methylphenoxy)ethanesulfonic acid Chemical compound CC1=CC(N)=C(N)C=C1OCCS(O)(=O)=O FKHUZRDQJTZMFB-UHFFFAOYSA-N 0.000 description 1
- FGHYCAHVTIVKDB-UHFFFAOYSA-N 2-amino-4-methyl-5-nitrobenzenesulfonic acid Chemical compound CC1=CC(N)=C(S(O)(=O)=O)C=C1[N+]([O-])=O FGHYCAHVTIVKDB-UHFFFAOYSA-N 0.000 description 1
- OQFSYHWITGFERZ-UHFFFAOYSA-N 2-bromoethanesulfonic acid Chemical compound OS(=O)(=O)CCBr OQFSYHWITGFERZ-UHFFFAOYSA-N 0.000 description 1
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- CBMSDILKECEMOT-UHFFFAOYSA-N potassium;2-methylpropan-1-olate Chemical compound [K+].CC(C)C[O-] CBMSDILKECEMOT-UHFFFAOYSA-N 0.000 description 1
- RWMKSKOZLCXHOK-UHFFFAOYSA-M potassium;butanoate Chemical compound [K+].CCCC([O-])=O RWMKSKOZLCXHOK-UHFFFAOYSA-M 0.000 description 1
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- MSGRFBKVMUKEGZ-UHFFFAOYSA-N quinoxalin-6-amine Chemical compound N1=CC=NC2=CC(N)=CC=C21 MSGRFBKVMUKEGZ-UHFFFAOYSA-N 0.000 description 1
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- 238000006467 substitution reaction Methods 0.000 description 1
- 150000003455 sulfinic acids Chemical class 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical class [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 150000003459 sulfonic acid esters Chemical class 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229940035024 thioglycerol Drugs 0.000 description 1
- 150000003585 thioureas Chemical class 0.000 description 1
- ILJSQTXMGCGYMG-UHFFFAOYSA-N triacetic acid Chemical compound CC(=O)CC(=O)CC(O)=O ILJSQTXMGCGYMG-UHFFFAOYSA-N 0.000 description 1
- XTTGYFREQJCEML-UHFFFAOYSA-N tributyl phosphite Chemical compound CCCCOP(OCCCC)OCCCC XTTGYFREQJCEML-UHFFFAOYSA-N 0.000 description 1
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 1
- CYTQBVOFDCPGCX-UHFFFAOYSA-N trimethyl phosphite Chemical compound COP(OC)OC CYTQBVOFDCPGCX-UHFFFAOYSA-N 0.000 description 1
- QOPBTFMUVTXWFF-UHFFFAOYSA-N tripropyl phosphite Chemical compound CCCOP(OCCC)OCCC QOPBTFMUVTXWFF-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/36—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems
- C07D241/38—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems with only hydrogen or carbon atoms directly attached to the ring nitrogen atoms
- C07D241/40—Benzopyrazines
- C07D241/42—Benzopyrazines with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
- G03C7/00—Multicolour photographic processes or agents therefor; Regeneration of such processing agents; Photosensitive materials for multicolour processes
- G03C7/28—Silver dye bleach processes; Materials therefor; Preparing or processing such materials
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Silver Salt Photography Or Processing Solution Therefor (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
- Luminescent Compositions (AREA)
Priority Applications (16)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH652176A CH621545A5 (en, 2012) | 1976-05-24 | 1976-05-24 | |
| IT4948777A IT1078291B (it) | 1976-05-24 | 1977-05-20 | Chinossaline e procedimento per la loro produzione ed applicazione |
| CA278,935A CA1100503A (en) | 1976-05-24 | 1977-05-20 | Quinoxalines and their use in photographic processes |
| DE2759813A DE2759813C2 (de) | 1976-05-24 | 1977-05-20 | Verfahren zur Herstellung farbphotographischer Bilder nach dem Silberfarbbleichverfahren und wässrige Zubereitung zur Farb- und/oder Silberbleichung |
| DE19772722776 DE2722776A1 (de) | 1976-05-24 | 1977-05-20 | Chinoxaline und deren verwendung in photographischen verfahren |
| FR7715787A FR2352806A1 (fr) | 1976-05-24 | 1977-05-23 | Quinoxalines, leur procede de preparation et leur application dans des procedes photographiques |
| ES459036A ES459036A1 (es) | 1976-05-24 | 1977-05-23 | Procedimiento para la preparacion de quinoxalinas. |
| AU25389/77A AU514121B2 (en) | 1976-05-24 | 1977-05-23 | Quinoxalines |
| AT366577A AT352527B (de) | 1976-05-24 | 1977-05-23 | Verfahren zur herstellung farbphotographischer bilder nach dem silberfarb- bleichverfahren |
| BE177784A BE854892A (fr) | 1976-05-24 | 1977-05-23 | Quinoxalines, leur procede de preparation et leur application dans desprocedes photographiques |
| GB21584/77A GB1532743A (en) | 1976-05-24 | 1977-05-23 | Quinoxalines and their use in photographic processes |
| JP52059501A JPS5830572B2 (ja) | 1976-05-24 | 1977-05-24 | 銀色素標白法によってカラ−写真画像を形成する方法 |
| NL7705703A NL7705703A (nl) | 1976-05-24 | 1977-05-24 | Werkwijze voor het bereiden van chinoxalinen en de toepassing van deze chinoxalinen in fotogra- fische werkwijzen. |
| US06/015,384 US4202698A (en) | 1976-05-24 | 1979-02-26 | Quinoxalines and their use in photographic processes |
| US06/088,727 US4323682A (en) | 1976-05-24 | 1979-10-26 | Quinoxalines and their use in photographic processes |
| JP17268980A JPS5697273A (en) | 1976-05-24 | 1980-12-09 | Quinoxaline and its manufacture |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH652176A CH621545A5 (en, 2012) | 1976-05-24 | 1976-05-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH621545A5 true CH621545A5 (en, 2012) | 1981-02-13 |
Family
ID=4310918
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH652176A CH621545A5 (en, 2012) | 1976-05-24 | 1976-05-24 |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US4323682A (en, 2012) |
| JP (2) | JPS5830572B2 (en, 2012) |
| AT (1) | AT352527B (en, 2012) |
| AU (1) | AU514121B2 (en, 2012) |
| BE (1) | BE854892A (en, 2012) |
| CA (1) | CA1100503A (en, 2012) |
| CH (1) | CH621545A5 (en, 2012) |
| DE (2) | DE2759813C2 (en, 2012) |
| ES (1) | ES459036A1 (en, 2012) |
| FR (1) | FR2352806A1 (en, 2012) |
| GB (1) | GB1532743A (en, 2012) |
| NL (1) | NL7705703A (en, 2012) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4304846A (en) * | 1979-02-09 | 1981-12-08 | Ciba-Geigy Ag | Method for processing silver dye-bleach materials |
| US4803209A (en) * | 1987-08-27 | 1989-02-07 | International Minerals & Chemical Corp. | Substituted 2,3-diphenyl-1,2-dihydroquinoxalines |
| TW290558B (en, 2012) * | 1994-04-28 | 1996-11-11 | Nissan Chemical Ind Ltd | |
| JP2002363169A (ja) * | 2001-06-08 | 2002-12-18 | Fujiyakuhin Co Ltd | 抗腫瘍活性を有する複素環化合物 |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE434413A (en, 2012) * | 1938-05-17 | |||
| BE631044A (en, 2012) * | 1962-04-12 | |||
| CH433980A (de) * | 1964-07-07 | 1967-04-15 | Ciba Geigy | Verwendung von Acylaminoverbindungen als Farbbleichkatalysatoren für das Silberfarbbleichverfahren |
| US3457074A (en) * | 1966-04-22 | 1969-07-22 | Eastman Kodak Co | Silver dye bleach element containing ballasted para-quinone as diffusion inhibitor |
| CH508226A (de) * | 1969-03-13 | 1971-05-31 | Ciba Geigy Ag | Verwendung von Chinoxalinen als Farbbleichkatalysatoren |
| CH553428A (de) * | 1970-09-04 | 1974-08-30 | Ciba Geigy Ag | Verwendung von chinoxalinen als wasserstoffuebertraeger. |
| CH543108A (de) * | 1970-09-04 | 1973-10-15 | Ciba Geigy Ag | Verwendung von Chinoxalinen in photographischen Verfahren |
| CH573448A5 (en, 2012) * | 1972-12-05 | 1976-03-15 | Ciba Geigy Ag | |
| US4001017A (en) * | 1972-12-05 | 1977-01-04 | Ciba-Geigy Ag | Process for the photopolymerization of ethylenically unsaturated compounds |
| CH584914A5 (en, 2012) * | 1973-10-12 | 1977-02-15 | Ciba Geigy Ag | |
| CH594912A5 (en, 2012) * | 1974-07-10 | 1978-01-31 | Ciba Geigy Ag |
-
1976
- 1976-05-24 CH CH652176A patent/CH621545A5/de not_active IP Right Cessation
-
1977
- 1977-05-20 CA CA278,935A patent/CA1100503A/en not_active Expired
- 1977-05-20 DE DE2759813A patent/DE2759813C2/de not_active Expired
- 1977-05-20 DE DE19772722776 patent/DE2722776A1/de active Granted
- 1977-05-23 AU AU25389/77A patent/AU514121B2/en not_active Expired
- 1977-05-23 FR FR7715787A patent/FR2352806A1/fr active Granted
- 1977-05-23 ES ES459036A patent/ES459036A1/es not_active Expired
- 1977-05-23 GB GB21584/77A patent/GB1532743A/en not_active Expired
- 1977-05-23 AT AT366577A patent/AT352527B/de not_active IP Right Cessation
- 1977-05-23 BE BE177784A patent/BE854892A/xx not_active IP Right Cessation
- 1977-05-24 NL NL7705703A patent/NL7705703A/xx not_active Application Discontinuation
- 1977-05-24 JP JP52059501A patent/JPS5830572B2/ja not_active Expired
-
1979
- 1979-10-26 US US06/088,727 patent/US4323682A/en not_active Expired - Lifetime
-
1980
- 1980-12-09 JP JP17268980A patent/JPS5697273A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5830572B2 (ja) | 1983-06-30 |
| DE2722776A1 (de) | 1977-12-08 |
| JPS6139307B2 (en, 2012) | 1986-09-03 |
| DE2722776C2 (en, 2012) | 1988-09-15 |
| AU2538977A (en) | 1978-11-30 |
| FR2352806A1 (fr) | 1977-12-23 |
| AT352527B (de) | 1979-09-25 |
| DE2759813C2 (de) | 1983-05-19 |
| CA1100503A (en) | 1981-05-05 |
| AU514121B2 (en) | 1981-01-29 |
| BE854892A (fr) | 1977-11-23 |
| ES459036A1 (es) | 1978-04-16 |
| ATA366577A (de) | 1979-02-15 |
| GB1532743A (en) | 1978-11-22 |
| JPS532486A (en) | 1978-01-11 |
| US4323682A (en) | 1982-04-06 |
| JPS5697273A (en) | 1981-08-05 |
| NL7705703A (nl) | 1977-11-28 |
| FR2352806B1 (en, 2012) | 1980-01-04 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |