DE2710285A1 - Verfahren zur herstellung von cumarinfarbstoffen - Google Patents
Verfahren zur herstellung von cumarinfarbstoffenInfo
- Publication number
- DE2710285A1 DE2710285A1 DE19772710285 DE2710285A DE2710285A1 DE 2710285 A1 DE2710285 A1 DE 2710285A1 DE 19772710285 DE19772710285 DE 19772710285 DE 2710285 A DE2710285 A DE 2710285A DE 2710285 A1 DE2710285 A1 DE 2710285A1
- Authority
- DE
- Germany
- Prior art keywords
- formula
- optionally substituted
- heterocyclic
- hydrogen
- parts
- Prior art date
- 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.)
- Ceased
Links
- 239000000975 dye Substances 0.000 title claims description 14
- 238000000034 method Methods 0.000 title claims description 11
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical compound C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 title claims description 9
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- PQMOXTJVIYEOQL-UHFFFAOYSA-N Cumarin Natural products CC(C)=CCC1=C(O)C(C(=O)C(C)CC)=C(O)C2=C1OC(=O)C=C2CCC PQMOXTJVIYEOQL-UHFFFAOYSA-N 0.000 title 1
- FSOGIJPGPZWNGO-UHFFFAOYSA-N Meomammein Natural products CCC(C)C(=O)C1=C(O)C(CC=C(C)C)=C(O)C2=C1OC(=O)C=C2CCC FSOGIJPGPZWNGO-UHFFFAOYSA-N 0.000 title 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 16
- -1 substituted alkyl radicals Chemical class 0.000 claims description 16
- 239000002253 acid Substances 0.000 claims description 9
- 125000000623 heterocyclic group Chemical group 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 7
- 125000001424 substituent group Chemical group 0.000 claims description 7
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 6
- ZMZSYUSDGRJZNT-UHFFFAOYSA-N 2-(1,3-benzothiazol-2-yl)acetonitrile Chemical compound C1=CC=C2SC(CC#N)=NC2=C1 ZMZSYUSDGRJZNT-UHFFFAOYSA-N 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- VRVRGVPWCUEOGV-UHFFFAOYSA-N 2-aminothiophenol Chemical class NC1=CC=CC=C1S VRVRGVPWCUEOGV-UHFFFAOYSA-N 0.000 claims description 4
- JXPDNDHCMMOJPC-UHFFFAOYSA-N 2-hydroxybutanedinitrile Chemical compound N#CC(O)CC#N JXPDNDHCMMOJPC-UHFFFAOYSA-N 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 4
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 4
- 235000001671 coumarin Nutrition 0.000 claims description 4
- 229960000956 coumarin Drugs 0.000 claims description 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 4
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 3
- 238000009833 condensation Methods 0.000 claims description 3
- 230000005494 condensation Effects 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 3
- 150000003254 radicals Chemical class 0.000 claims description 3
- 239000011541 reaction mixture Substances 0.000 claims description 3
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
- 125000005194 alkoxycarbonyloxy group Chemical group 0.000 claims description 2
- 150000005840 aryl radicals Chemical class 0.000 claims description 2
- 230000003197 catalytic effect Effects 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 125000004122 cyclic group Chemical group 0.000 claims description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 2
- 239000011707 mineral Substances 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 125000004434 sulfur atom Chemical group 0.000 claims description 2
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- 125000003806 alkyl carbonyl amino group Chemical group 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
- 150000002391 heterocyclic compounds Chemical class 0.000 claims 1
- 238000000746 purification Methods 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 239000000203 mixture Substances 0.000 description 8
- 239000002904 solvent Substances 0.000 description 7
- 125000000217 alkyl group Chemical group 0.000 description 5
- YXHVGMQJXJAUAR-UHFFFAOYSA-N 2-(diethylaminooxy)benzaldehyde Chemical compound CCN(CC)OC1=CC=CC=C1C=O YXHVGMQJXJAUAR-UHFFFAOYSA-N 0.000 description 4
- 150000001299 aldehydes Chemical class 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 239000001632 sodium acetate Substances 0.000 description 3
- 235000017281 sodium acetate Nutrition 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
- MDRLVZSRYQCOPC-UHFFFAOYSA-N 2-(1,3-benzoxazol-2-yl)propanenitrile Chemical compound C1=CC=C2OC(C(C#N)C)=NC2=C1 MDRLVZSRYQCOPC-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 125000002252 acyl group Chemical group 0.000 description 2
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 238000005580 one pot reaction Methods 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
- AVQQQNCBBIEMEU-UHFFFAOYSA-N 1,1,3,3-tetramethylurea Chemical compound CN(C)C(=O)N(C)C AVQQQNCBBIEMEU-UHFFFAOYSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- MSSDTZLYNMFTKN-UHFFFAOYSA-N 1-Piperazinecarboxaldehyde Chemical compound O=CN1CCNCC1 MSSDTZLYNMFTKN-UHFFFAOYSA-N 0.000 description 1
- WGCYRFWNGRMRJA-UHFFFAOYSA-N 1-ethylpiperazine Chemical compound CCN1CCNCC1 WGCYRFWNGRMRJA-UHFFFAOYSA-N 0.000 description 1
- JOUFEXYUGSESJE-UHFFFAOYSA-N 2-(1,3-benzothiazol-2-yl)-2,2-dichloroacetonitrile Chemical compound C1=CC=C2SC(C(Cl)(C#N)Cl)=NC2=C1 JOUFEXYUGSESJE-UHFFFAOYSA-N 0.000 description 1
- XBRJMRSUWOMPPI-UHFFFAOYSA-N 2-(1,3-benzothiazol-2-yl)-2-chloroacetonitrile Chemical compound C1=CC=C2SC(C(C#N)Cl)=NC2=C1 XBRJMRSUWOMPPI-UHFFFAOYSA-N 0.000 description 1
- SWNMCRPDVLARDN-UHFFFAOYSA-N 2-(1,3-benzothiazol-2-yl)-2-methylpropanenitrile Chemical compound C1=CC=C2SC(C(C)(C#N)C)=NC2=C1 SWNMCRPDVLARDN-UHFFFAOYSA-N 0.000 description 1
- KPPDWDYVGGNHDH-UHFFFAOYSA-N 2-(1,3-benzothiazol-2-yl)-2-nitroacetonitrile Chemical compound C1=CC=C2SC(C(C#N)[N+](=O)[O-])=NC2=C1 KPPDWDYVGGNHDH-UHFFFAOYSA-N 0.000 description 1
- MKXAJHCZWWZMCK-UHFFFAOYSA-N 2-(1,3-benzothiazol-2-yl)-3-chloropropanenitrile Chemical compound C1=CC=C2SC(C(C#N)CCl)=NC2=C1 MKXAJHCZWWZMCK-UHFFFAOYSA-N 0.000 description 1
- SIMWFXSMDQBKED-UHFFFAOYSA-N 2-(1,3-benzothiazol-2-yl)acetamide Chemical class C1=CC=C2SC(CC(=O)N)=NC2=C1 SIMWFXSMDQBKED-UHFFFAOYSA-N 0.000 description 1
- HBFODRKNDXOVTJ-UHFFFAOYSA-N 2-(1,3-benzothiazol-2-yl)propanenitrile Chemical compound C1=CC=C2SC(C(C#N)C)=NC2=C1 HBFODRKNDXOVTJ-UHFFFAOYSA-N 0.000 description 1
- DYFOZNOSAPXUGD-UHFFFAOYSA-N 2-(1,3-benzothiazol-2-yl)propanoic acid Chemical class C1=CC=C2SC(C(C(O)=O)C)=NC2=C1 DYFOZNOSAPXUGD-UHFFFAOYSA-N 0.000 description 1
- ZYRXUNMCONQMJR-UHFFFAOYSA-N 2-(1,3-benzoxazol-2-yl)-2,2-dichloroacetonitrile Chemical compound C1=CC=C2OC(C(Cl)(C#N)Cl)=NC2=C1 ZYRXUNMCONQMJR-UHFFFAOYSA-N 0.000 description 1
- VNMKWZBURQHRLC-UHFFFAOYSA-N 2-(1,3-benzoxazol-2-yl)-2-methylpropanenitrile Chemical compound C1=CC=C2OC(C(C)(C#N)C)=NC2=C1 VNMKWZBURQHRLC-UHFFFAOYSA-N 0.000 description 1
- LQSLYMXFUJMFRG-UHFFFAOYSA-N 2-(1,3-benzoxazol-2-yl)-2-nitroacetonitrile Chemical compound C1=CC=C2OC(C(C#N)[N+](=O)[O-])=NC2=C1 LQSLYMXFUJMFRG-UHFFFAOYSA-N 0.000 description 1
- RCUFVNYFFLUNMI-UHFFFAOYSA-N 2-(1,3-benzoxazol-2-yl)-2-phenylacetonitrile Chemical compound N=1C2=CC=CC=C2OC=1C(C#N)C1=CC=CC=C1 RCUFVNYFFLUNMI-UHFFFAOYSA-N 0.000 description 1
- KYRRAGIOAZNKGO-UHFFFAOYSA-N 2-(1,3-benzoxazol-2-yl)acetamide Chemical class C1=CC=C2OC(CC(=O)N)=NC2=C1 KYRRAGIOAZNKGO-UHFFFAOYSA-N 0.000 description 1
- NGUJPJCKRWSDCS-UHFFFAOYSA-N 2-(1,3-benzoxazol-2-yl)acetonitrile Chemical compound C1=CC=C2OC(CC#N)=NC2=C1 NGUJPJCKRWSDCS-UHFFFAOYSA-N 0.000 description 1
- WYBQULDLSLGPQY-UHFFFAOYSA-N 2-(5-methyl-1,3-benzoxazol-2-yl)acetonitrile Chemical compound CC1=CC=C2OC(CC#N)=NC2=C1 WYBQULDLSLGPQY-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- POGDFZRQLHGZJM-UHFFFAOYSA-N 2-benzo[e][1,3]benzoxazol-2-ylacetonitrile Chemical compound C1=CC=C2C(N=C(O3)CC#N)=C3C=CC2=C1 POGDFZRQLHGZJM-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 125000003047 N-acetyl group Chemical group 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 125000004442 acylamino group Chemical group 0.000 description 1
- 125000004423 acyloxy group Chemical group 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000003282 alkyl amino group Chemical group 0.000 description 1
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 239000011260 aqueous acid Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 1
- 229940106681 chloroacetic acid Drugs 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229920001577 copolymer Chemical class 0.000 description 1
- 125000004663 dialkyl amino group Chemical group 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 150000002168 ethanoic acid esters Chemical class 0.000 description 1
- JVPVZDUFKWWIAQ-UHFFFAOYSA-N ethyl 3-(1,3-benzoxazol-2-yl)-3-cyanopropanoate Chemical compound C1=CC=C2OC(C(C#N)CC(=O)OCC)=NC2=C1 JVPVZDUFKWWIAQ-UHFFFAOYSA-N 0.000 description 1
- DUBPDLQMQGFHOY-UHFFFAOYSA-N ethyl 4-(1,3-benzoxazol-2-yl)-4-cyanobutanoate Chemical compound C1=CC=C2OC(C(C#N)CCC(=O)OCC)=NC2=C1 DUBPDLQMQGFHOY-UHFFFAOYSA-N 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- CUONGYYJJVDODC-UHFFFAOYSA-N malononitrile Chemical compound N#CCC#N CUONGYYJJVDODC-UHFFFAOYSA-N 0.000 description 1
- 238000010327 methods by industry Methods 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- RAHZWNYVWXNFOC-UHFFFAOYSA-N sulfur dioxide Inorganic materials O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 229950011008 tetrachloroethylene Drugs 0.000 description 1
- WQWBWTCQPZVQRC-UHFFFAOYSA-N tris(dimethylamino) phosphate Chemical compound CN(C)OP(=O)(ON(C)C)ON(C)C WQWBWTCQPZVQRC-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B57/00—Other synthetic dyes of known constitution
- C09B57/02—Coumarine dyes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH303676 | 1976-03-11 | ||
| CH303576A CH599313A5 (en) | 1976-03-11 | 1976-03-11 | Fluorescent coumarin dyes prodn. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2710285A1 true DE2710285A1 (de) | 1977-09-15 |
Family
ID=25691994
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19772710285 Ceased DE2710285A1 (de) | 1976-03-11 | 1977-03-09 | Verfahren zur herstellung von cumarinfarbstoffen |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US4146712A (ref) |
| JP (1) | JPS6021190B2 (ref) |
| DE (1) | DE2710285A1 (ref) |
| FR (1) | FR2343786A1 (ref) |
| GB (1) | GB1573632A (ref) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0030703A1 (de) * | 1979-12-14 | 1981-06-24 | BASF Aktiengesellschaft | Verfahren zur Herstellung von Cumarinverbindungen |
| EP0428939A3 (en) * | 1989-11-21 | 1992-03-25 | Bayer Ag | Cumarin derivatives, process for their preparation, their use and thiazolylacetic acid derivatives as intermediate |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2807761A1 (de) * | 1978-02-23 | 1979-08-30 | Basf Ag | Cumarinderivate |
| EP0023022B1 (de) * | 1979-07-20 | 1984-04-11 | Ciba-Geigy Ag | Cumarinverbindungen, Verfahren zu deren Herstellung sowie die dafür verwendeten Zwischenprodukte an sich und ihre Verwendung zum Färben oder Bedrucken von Textilien |
| US4656267A (en) * | 1983-09-29 | 1987-04-07 | Ortho Pharmaceutical Corporation | Substituted 2(1H)-quinazolinone-1-alkanoic acids and esters |
| DK1737492T3 (da) * | 2004-04-16 | 2013-03-11 | Bredent Medical Gmbh & Co Kg | Præparat til fotodynamisk bekæmpelse af mikroorganismer samt anvendelse af præparatet |
| US20070254349A1 (en) * | 2004-04-16 | 2007-11-01 | Helbo Photodynamic Systems Gmbh & Co.Kg | Preparation for the Photodynamic Control of Micro-Organisms and Use Thereof |
| WO2008021623A1 (en) * | 2006-08-10 | 2008-02-21 | Gambro Bct, Inc. | Method and apparatus for recirculating elutriation fluids |
| CN101368004B (zh) * | 2008-09-25 | 2011-08-31 | 浙江工业大学 | 一种香豆素类荧光染料的合成方法 |
| CN103319475B (zh) * | 2013-02-01 | 2015-07-08 | 山西大同大学 | 一种n’-(苯并噻唑基)-3-甲酰胺-7-n,n-二乙基-香豆素及其制备方法和应用 |
| US9810700B1 (en) | 2017-05-31 | 2017-11-07 | Aat Bioquest, Inc. | Fluorogenic calcium ion indicators and methods of using the same |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1098125B (de) * | 1958-06-19 | 1961-01-26 | Geigy Ag J R | Verfahren zur Herstellung von fluoreszierenden Verbindungen |
| DE2364478A1 (de) * | 1972-12-25 | 1974-07-04 | Sumitomo Chemical Co | Verfahren zur herstellung von cumarinfarbstoffen |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1543933A (en) * | 1975-07-02 | 1979-04-11 | Basf Ag | Dyes of the coumarin series |
-
1977
- 1977-02-22 US US05/770,493 patent/US4146712A/en not_active Expired - Lifetime
- 1977-03-09 DE DE19772710285 patent/DE2710285A1/de not_active Ceased
- 1977-03-10 GB GB10223/77A patent/GB1573632A/en not_active Expired
- 1977-03-10 FR FR7707134A patent/FR2343786A1/fr active Granted
- 1977-03-11 JP JP52026122A patent/JPS6021190B2/ja not_active Expired
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1098125B (de) * | 1958-06-19 | 1961-01-26 | Geigy Ag J R | Verfahren zur Herstellung von fluoreszierenden Verbindungen |
| DE2364478A1 (de) * | 1972-12-25 | 1974-07-04 | Sumitomo Chemical Co | Verfahren zur herstellung von cumarinfarbstoffen |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0030703A1 (de) * | 1979-12-14 | 1981-06-24 | BASF Aktiengesellschaft | Verfahren zur Herstellung von Cumarinverbindungen |
| EP0428939A3 (en) * | 1989-11-21 | 1992-03-25 | Bayer Ag | Cumarin derivatives, process for their preparation, their use and thiazolylacetic acid derivatives as intermediate |
| US5300656A (en) * | 1989-11-21 | 1994-04-05 | Bayer Aktiengesellschaft | Coumarin derivatives, process for their preparation, their use and thiazolyl acetic acid derivatives as intermediates |
Also Published As
| Publication number | Publication date |
|---|---|
| GB1573632A (en) | 1980-08-28 |
| JPS52109525A (en) | 1977-09-13 |
| FR2343786A1 (fr) | 1977-10-07 |
| JPS6021190B2 (ja) | 1985-05-25 |
| FR2343786B1 (ref) | 1980-01-11 |
| US4146712A (en) | 1979-03-27 |
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| Date | Code | Title | Description |
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| 8110 | Request for examination paragraph 44 | ||
| 8131 | Rejection |