DE2304201C2 - 2-Aminothiophene - Google Patents
2-AminothiopheneInfo
- Publication number
- DE2304201C2 DE2304201C2 DE19732304201 DE2304201A DE2304201C2 DE 2304201 C2 DE2304201 C2 DE 2304201C2 DE 19732304201 DE19732304201 DE 19732304201 DE 2304201 A DE2304201 A DE 2304201A DE 2304201 C2 DE2304201 C2 DE 2304201C2
- Authority
- DE
- Germany
- Prior art keywords
- parts
- nitrothiophene
- amino
- mixture
- acetylamino
- 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.)
- Expired
Links
- GLQWRXYOTXRDNH-UHFFFAOYSA-N thiophen-2-amine Chemical class NC1=CC=CS1 GLQWRXYOTXRDNH-UHFFFAOYSA-N 0.000 title description 6
- -1 cyano, aminocarbonyl Chemical group 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
- 125000006501 nitrophenyl group Chemical group 0.000 claims 1
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims 1
- WFDIJRYMOXRFFG-UHFFFAOYSA-N acetic acid anhydride Natural products CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 34
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 28
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 27
- 239000000203 mixture Substances 0.000 description 27
- 150000001875 compounds Chemical class 0.000 description 17
- 238000006396 nitration reaction Methods 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000009835 boiling Methods 0.000 description 6
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 6
- 230000007062 hydrolysis Effects 0.000 description 6
- 238000006460 hydrolysis reaction Methods 0.000 description 6
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 6
- 239000007787 solid Substances 0.000 description 5
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 4
- 125000002843 carboxylic acid group Chemical group 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 3
- 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 3
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 3
- 239000000987 azo dye Substances 0.000 description 3
- 125000004093 cyano group Chemical group *C#N 0.000 description 3
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 3
- DSHKXMXRBKLFRU-UHFFFAOYSA-N ethyl 2-acetamidothiophene-3-carboxylate Chemical compound CCOC(=O)C=1C=CSC=1NC(C)=O DSHKXMXRBKLFRU-UHFFFAOYSA-N 0.000 description 3
- 235000019253 formic acid Nutrition 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 229910017604 nitric acid Inorganic materials 0.000 description 3
- 150000002923 oximes Chemical class 0.000 description 3
- BBMCTIGTTCKYKF-UHFFFAOYSA-N 1-heptanol Chemical compound CCCCCCCO BBMCTIGTTCKYKF-UHFFFAOYSA-N 0.000 description 2
- CFKZMYPOJOKAAD-UHFFFAOYSA-N 2-amino-5-nitrothiophene-3-carbonitrile Chemical compound NC=1SC([N+]([O-])=O)=CC=1C#N CFKZMYPOJOKAAD-UHFFFAOYSA-N 0.000 description 2
- IICFGCMPQMPNRU-UHFFFAOYSA-N 2-amino-5-nitrothiophene-3-carboxylic acid Chemical compound NC=1SC([N+]([O-])=O)=CC=1C(O)=O IICFGCMPQMPNRU-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 2
- 150000002148 esters Chemical group 0.000 description 2
- 238000005530 etching Methods 0.000 description 2
- IAFPZBCUVMQVBI-UHFFFAOYSA-N ethyl 2-acetamido-5-nitrothiophene-3-carboxylate Chemical compound CCOC(=O)C=1C=C([N+]([O-])=O)SC=1NC(C)=O IAFPZBCUVMQVBI-UHFFFAOYSA-N 0.000 description 2
- CTHOBBRGWQVVGK-UHFFFAOYSA-N ethyl 2-amino-5-cyano-4-methylthiophene-3-carboxylate Chemical compound CCOC(=O)C1=C(N)SC(C#N)=C1C CTHOBBRGWQVVGK-UHFFFAOYSA-N 0.000 description 2
- UXDKVBJDZDRIKL-UHFFFAOYSA-N ethyl 2-amino-5-nitrothiophene-3-carboxylate Chemical compound CCOC(=O)C=1C=C([N+]([O-])=O)SC=1N UXDKVBJDZDRIKL-UHFFFAOYSA-N 0.000 description 2
- MKJQYFVTEPGXIE-UHFFFAOYSA-N ethyl 2-aminothiophene-3-carboxylate Chemical compound CCOC(=O)C=1C=CSC=1N MKJQYFVTEPGXIE-UHFFFAOYSA-N 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- JIKUXBYRTXDNIY-UHFFFAOYSA-N n-methyl-n-phenylformamide Chemical compound O=CN(C)C1=CC=CC=C1 JIKUXBYRTXDNIY-UHFFFAOYSA-N 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000001632 sodium acetate Substances 0.000 description 2
- 235000017281 sodium acetate Nutrition 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- 229930192474 thiophene Natural products 0.000 description 2
- 239000001677 (2R,5R)-1,4-dithiane-2,5-diol Substances 0.000 description 1
- YUIOPHXTILULQC-UHFFFAOYSA-N 1,4-Dithiane-2,5-diol Chemical compound OC1CSC(O)CS1 YUIOPHXTILULQC-UHFFFAOYSA-N 0.000 description 1
- ZFCFFNGBCVAUDE-UHFFFAOYSA-N 2-(benzenesulfonyl)acetonitrile Chemical compound N#CCS(=O)(=O)C1=CC=CC=C1 ZFCFFNGBCVAUDE-UHFFFAOYSA-N 0.000 description 1
- XVGHZFWFGXDIOU-UHFFFAOYSA-N 2-aminothiophene-3-carbonitrile Chemical compound NC=1SC=CC=1C#N XVGHZFWFGXDIOU-UHFFFAOYSA-N 0.000 description 1
- MWMGJXBRRZFUAW-UHFFFAOYSA-N 2-formamido-5-nitrothiophene-3-carboxylic acid Chemical compound OC(=O)C=1C=C([N+]([O-])=O)SC=1NC=O MWMGJXBRRZFUAW-UHFFFAOYSA-N 0.000 description 1
- ZWSJWGDWLCBNLV-UHFFFAOYSA-N 2-formamidothiophene-3-carboxylic acid Chemical compound OC(=O)C=1C=CSC=1NC=O ZWSJWGDWLCBNLV-UHFFFAOYSA-N 0.000 description 1
- CBIBOYBKSIQGPR-UHFFFAOYSA-N 2-methylpropyl 2-acetamidothiophene-3-carboxylate Chemical compound CC(C)COC(=O)C=1C=CSC=1NC(C)=O CBIBOYBKSIQGPR-UHFFFAOYSA-N 0.000 description 1
- GGABEWSRMITGQF-UHFFFAOYSA-N 2-methylpropyl 2-amino-5-nitrothiophene-3-carboxylate Chemical compound CC(C)COC(=O)C=1C=C([N+]([O-])=O)SC=1N GGABEWSRMITGQF-UHFFFAOYSA-N 0.000 description 1
- JIZRGGUCOQKGQD-UHFFFAOYSA-N 2-nitrothiophene Chemical compound [O-][N+](=O)C1=CC=CS1 JIZRGGUCOQKGQD-UHFFFAOYSA-N 0.000 description 1
- XGIMMKDOEWXVKN-UHFFFAOYSA-N 3-(benzenesulfonyl)-5-nitrothiophen-2-amine Chemical compound S1C([N+]([O-])=O)=CC(S(=O)(=O)C=2C=CC=CC=2)=C1N XGIMMKDOEWXVKN-UHFFFAOYSA-N 0.000 description 1
- 125000003047 N-acetyl group Chemical group 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 1
- DYRDKSSFIWVSNM-UHFFFAOYSA-N acetoacetanilide Chemical compound CC(=O)CC(=O)NC1=CC=CC=C1 DYRDKSSFIWVSNM-UHFFFAOYSA-N 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 230000021736 acetylation Effects 0.000 description 1
- 238000006640 acetylation reaction Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 125000004442 acylamino group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- BSGKDKPEIZHXEI-UHFFFAOYSA-N butyl 2-amino-5-nitrothiophene-3-carboxylate Chemical compound CCCCOC(=O)C=1C=C([N+]([O-])=O)SC=1N BSGKDKPEIZHXEI-UHFFFAOYSA-N 0.000 description 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 1
- 125000003262 carboxylic acid ester group Chemical group [H]C([H])([*:2])OC(=O)C([H])([H])[*:1] 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000020176 deacylation Effects 0.000 description 1
- 238000005947 deacylation reaction Methods 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- ZHBROGDSPSWMPO-UHFFFAOYSA-N ethyl 2-acetamido-4-methylthiophene-3-carboxylate Chemical compound CCOC(=O)C=1C(C)=CSC=1NC(C)=O ZHBROGDSPSWMPO-UHFFFAOYSA-N 0.000 description 1
- BTVGAQBRKLATQO-UHFFFAOYSA-N ethyl 2-acetamido-4-phenylthiophene-3-carboxylate Chemical compound CCOC(=O)C1=C(NC(C)=O)SC=C1C1=CC=CC=C1 BTVGAQBRKLATQO-UHFFFAOYSA-N 0.000 description 1
- JWOJPJJBPNACDX-UHFFFAOYSA-N ethyl 2-amino-4-methyl-5-nitrothiophene-3-carboxylate Chemical compound CCOC(=O)C1=C(N)SC([N+]([O-])=O)=C1C JWOJPJJBPNACDX-UHFFFAOYSA-N 0.000 description 1
- NLUSXEXJKKHXEX-UHFFFAOYSA-N ethyl 2-amino-5-nitro-4-(2-nitrophenyl)thiophene-3-carboxylate Chemical compound CCOC(=O)C1=C(N)SC([N+]([O-])=O)=C1C1=CC=CC=C1[N+]([O-])=O NLUSXEXJKKHXEX-UHFFFAOYSA-N 0.000 description 1
- CVHZZPREEGCQBR-UHFFFAOYSA-N ethyl 2-amino-5-nitro-4-(4-nitrophenyl)thiophene-3-carboxylate Chemical compound CCOC(=O)C1=C(N)SC([N+]([O-])=O)=C1C1=CC=C([N+]([O-])=O)C=C1 CVHZZPREEGCQBR-UHFFFAOYSA-N 0.000 description 1
- OVACPXHJGKCAAK-UHFFFAOYSA-N ethyl 2-amino-5-nitro-4-phenylthiophene-3-carboxylate Chemical group CCOC(=O)C1=C(N)SC([N+]([O-])=O)=C1C1=CC=CC=C1 OVACPXHJGKCAAK-UHFFFAOYSA-N 0.000 description 1
- ZIUSEGSNTOUIPT-UHFFFAOYSA-N ethyl 2-cyanoacetate Chemical compound CCOC(=O)CC#N ZIUSEGSNTOUIPT-UHFFFAOYSA-N 0.000 description 1
- OQHQFKVRKHBMIS-UHFFFAOYSA-N ethyl 2-formamidothiophene-3-carboxylate Chemical compound CCOC(=O)C=1C=CSC=1NC=O OQHQFKVRKHBMIS-UHFFFAOYSA-N 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- MLAPMAXKPXBHKO-UHFFFAOYSA-N methyl 2-acetamidothiophene-3-carboxylate Chemical compound COC(=O)C=1C=CSC=1NC(C)=O MLAPMAXKPXBHKO-UHFFFAOYSA-N 0.000 description 1
- OVLUSSXPOANNKZ-UHFFFAOYSA-N methyl 2-amino-5-nitrothiophene-3-carboxylate Chemical compound COC(=O)C=1C=C([N+]([O-])=O)SC=1N OVLUSSXPOANNKZ-UHFFFAOYSA-N 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- YGHZTDCKVMBFIF-UHFFFAOYSA-N n-(3-cyanothiophen-2-yl)formamide Chemical compound O=CNC=1SC=CC=1C#N YGHZTDCKVMBFIF-UHFFFAOYSA-N 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 150000003577 thiophenes Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D333/42—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms with nitro or nitroso radicals directly attached to ring carbon atoms
- C07D333/44—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms with nitro or nitroso radicals directly attached to ring carbon atoms attached in position 5
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- 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
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/0025—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds
- C09B29/0059—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds the heterocyclic ring containing only sulfur as heteroatom
-
- 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
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/06—Monoazo dyes prepared by diazotising and coupling from coupling components containing amino as the only directing group
-
- 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
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/06—Monoazo dyes prepared by diazotising and coupling from coupling components containing amino as the only directing group
- C09B29/08—Amino benzenes
-
- 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
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/06—Monoazo dyes prepared by diazotising and coupling from coupling components containing amino as the only directing group
- C09B29/08—Amino benzenes
- C09B29/0805—Amino benzenes free of acid groups
-
- 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
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/06—Monoazo dyes prepared by diazotising and coupling from coupling components containing amino as the only directing group
- C09B29/08—Amino benzenes
- C09B29/0805—Amino benzenes free of acid groups
- C09B29/0807—Amino benzenes free of acid groups characterised by the amino group
-
- 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
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/34—Monoazo dyes prepared by diazotising and coupling from other coupling components
- C09B29/36—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds
- C09B29/3604—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom
- C09B29/3617—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a six-membered heterocyclic with only one nitrogen as heteroatom
- C09B29/3621—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a six-membered heterocyclic with only one nitrogen as heteroatom from a pyridine ring
- C09B29/3626—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a six-membered heterocyclic with only one nitrogen as heteroatom from a pyridine ring from a pyridine ring containing one or more hydroxyl groups (or = O)
- C09B29/3634—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a six-membered heterocyclic with only one nitrogen as heteroatom from a pyridine ring from a pyridine ring containing one or more hydroxyl groups (or = O) from diazotized heterocyclic rings
-
- 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
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/34—Monoazo dyes prepared by diazotising and coupling from other coupling components
- C09B29/36—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds
- C09B29/3695—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing other heterocyclic compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB404672A GB1394365A (en) | 1972-01-28 | 1972-01-28 | Disperse azo dyestuffs |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2304201A1 DE2304201A1 (de) | 1973-08-02 |
| DE2304201C2 true DE2304201C2 (de) | 1982-04-08 |
Family
ID=9769733
Family Applications (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19732304201 Expired DE2304201C2 (de) | 1972-01-28 | 1973-01-29 | 2-Aminothiophene |
| DE19732304202 Expired DE2304202C2 (de) | 1972-01-28 | 1973-01-29 | Disperse Monoazofarbstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung |
| DE19732304218 Expired DE2304218C2 (de) | 1972-01-28 | 1973-01-29 | Disperse Azofarbstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung zum Färben von synthetischen Textilmaterialien |
| DE19732304203 Expired DE2304203C2 (de) | 1972-01-28 | 1973-01-29 | Disperse Monoazofarbstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung zum Färben von Textilmaterialien |
Family Applications After (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19732304202 Expired DE2304202C2 (de) | 1972-01-28 | 1973-01-29 | Disperse Monoazofarbstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung |
| DE19732304218 Expired DE2304218C2 (de) | 1972-01-28 | 1973-01-29 | Disperse Azofarbstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung zum Färben von synthetischen Textilmaterialien |
| DE19732304203 Expired DE2304203C2 (de) | 1972-01-28 | 1973-01-29 | Disperse Monoazofarbstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung zum Färben von Textilmaterialien |
Country Status (11)
Families Citing this family (40)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4079050A (en) * | 1972-01-28 | 1978-03-14 | Imperial Chemical Industries Limited | Disperse monoazo dyestuffs containing a thiophene residue |
| NL7309098A (enrdf_load_stackoverflow) * | 1972-07-04 | 1974-01-08 | ||
| CH554395A (de) * | 1972-07-11 | 1974-09-30 | Sandoz Ag | Verfahren zur herstellung in wasser schwer loeslicher azoverbindungen. |
| AR204517A1 (es) * | 1972-12-01 | 1976-02-12 | Sandoz Ag | Procedimiento para obtener compuestos de 5-ciano-2-amino-tiofenos |
| CH584257A5 (enrdf_load_stackoverflow) * | 1973-09-06 | 1977-01-31 | Sandoz Ag | |
| US4140683A (en) * | 1976-02-23 | 1979-02-20 | Eastman Kodak Company | Dyes from thienylazo compounds and cyclohexylaminoacylanilide couplers |
| GB1583377A (en) * | 1977-04-25 | 1981-01-28 | Ici Ltd | Disperse azo dyestuffs derived from a 2-aminothiophene-5-aldehyde |
| US4204991A (en) * | 1977-10-25 | 1980-05-27 | G. D. Searle & Co. | Sarcosine1 dehydroalanine8 angiotensin II derivatives |
| DE2759103C2 (de) * | 1977-12-30 | 1986-10-09 | Bayer Ag, 5090 Leverkusen | Azofarbstoffe und deren Verwendung |
| DE3007518A1 (de) * | 1980-02-28 | 1981-09-17 | Cassella Ag, 6000 Frankfurt | Wasserunloesliche azofarbstoffe, verfahren zu ihrer herstellung und verwendung zum faerben und bedrucken von synthetischem, hydrophobem fasermaterial |
| US4400318A (en) * | 1980-05-19 | 1983-08-23 | Eastman Kodak Company | Substituted 5-acyl-3-carbamoyl-2-thienyl azo dyes with aniline, tetrahydroquinoline, and benzomorpholine couplers, process of manufacture, and polyamide testile materials dyed therewith |
| JPS57141451A (en) * | 1981-02-26 | 1982-09-01 | Sumitomo Chem Co Ltd | Monoazo dye and production thereof |
| US4385104A (en) | 1981-04-29 | 1983-05-24 | Eastman Kodak Company | Photographic products and processes employing novel nondiffusible 6-(2-thienylazo)-3-pyridinol cyan dye-releasing compounds and precursors thereof |
| US4396546A (en) | 1981-04-29 | 1983-08-02 | Eastman Kodak Company | Photographic products and processes employing novel nondiffusible 6-(2-thienylazo)-3-pyridinol cyan dye-releasing compounds and precursors thereof |
| JPS5924754A (ja) * | 1982-07-30 | 1984-02-08 | Gosei Senriyou Gijutsu Kenkyu Kumiai | モノアゾ化合物及びそれを用いる染色法 |
| JPS5922964A (ja) * | 1982-07-30 | 1984-02-06 | Hitachi Ltd | アゾ系多色性色素を含む液晶組成物 |
| JPS5996165A (ja) * | 1982-11-22 | 1984-06-02 | Gosei Senriyou Gijutsu Kenkyu Kumiai | 合成繊維用モノアゾ染料 |
| DE3402026A1 (de) * | 1984-01-21 | 1985-07-25 | Basf Ag, 6700 Ludwigshafen | Neue 2-aminothiophenderivate |
| US4568738A (en) * | 1984-03-19 | 1986-02-04 | Eastman Kodak Company | Thiophen-2-ylazopyrazole compounds as colorants for textile fibers |
| US4507407A (en) * | 1984-06-25 | 1985-03-26 | Milliken Research Corporation | Process for in situ coloration of thermosetting resins |
| CA1243669A (en) * | 1984-06-25 | 1988-10-25 | Edward W. Kluger | Reactive colorants |
| DE3507421A1 (de) * | 1985-03-02 | 1986-09-04 | Basf Ag, 6700 Ludwigshafen | Thiophenderivate |
| DE3663945D1 (en) * | 1985-03-02 | 1989-07-20 | Basf Ag | Thiophene derivatives |
| DE3510410A1 (de) * | 1985-03-22 | 1986-09-25 | Bayer Ag, 5090 Leverkusen | Azofarbstoffe |
| DE3512760A1 (de) * | 1985-04-10 | 1986-10-23 | Basf Ag, 6700 Ludwigshafen | Azofarbstoffe mit thiophen-diazokomponenten |
| DE3528759A1 (de) * | 1985-08-10 | 1987-02-19 | Basf Ag | Heterocyclische azofarbstoffe |
| DE3639942A1 (de) * | 1986-11-22 | 1988-06-01 | Basf Ag | Thiophenazofarbstoffe |
| US4751254A (en) * | 1987-01-20 | 1988-06-14 | Milliken Research Corporation | Process for in situ coloration of thermosetting resins |
| DE3876313T2 (de) * | 1987-06-29 | 1993-04-01 | Ici Plc | Dispersionsfarbstoffe. |
| US5052380A (en) * | 1989-07-07 | 1991-10-01 | Minnesota Mining And Manufacturing Company | Colored orthopedic resins and orthopedic casting materials incorporating same |
| DE69209725T2 (de) * | 1991-06-11 | 1996-10-31 | Dystar Japan Ltd | Monoazofarbstoff |
| GB9215777D0 (en) * | 1992-07-24 | 1992-09-09 | Ici Plc | Disperse dyes |
| GB9219418D0 (en) * | 1992-09-14 | 1992-10-28 | Ici Plc | Disperse dyes |
| TW324021B (en) * | 1994-03-08 | 1998-01-01 | Daistar Japan Kk | Mono-azo dyestuff |
| KR960031548A (ko) * | 1995-02-20 | 1996-09-17 | 고사이 아키오 | 모노아조 화합물 및 이 화합물을 사용하는 소수성 섬유재료의 염색 또는 날염방법 |
| GB9515175D0 (en) * | 1995-07-24 | 1995-09-20 | Zeneca Ltd | Azothiophenes |
| GB9608489D0 (en) * | 1996-04-25 | 1996-07-03 | Zeneca Ltd | Compositions, processes and uses |
| JP7355395B2 (ja) * | 2018-12-26 | 2023-10-03 | 健 緒方 | ソーシャルアーカイビングサービスのための方法及びシステム |
| US12195703B2 (en) * | 2020-03-02 | 2025-01-14 | Milliken & Company | Composition comprising hueing agent |
| CN112341430A (zh) * | 2020-11-11 | 2021-02-09 | 嘉禾宜事达（沈阳）化学有限公司 | 单偶氮化合物及其制备方法和应用 |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA895863A (en) * | 1972-03-21 | A. Weaver Max | Azo compound containing a triazolylthio group | |
| DE1079759B (de) * | 1954-04-05 | 1960-04-14 | Eastman Kodak Co | Verfahren zur Herstellung von Monoazofarbstoffen |
| US2805218A (en) * | 1954-04-05 | 1957-09-03 | Eastman Kodak Co | 2-amino-3-nitro-5-acylthiophene azo dye compounds |
| FR1139567A (fr) * | 1954-04-05 | 1957-07-02 | Eastman Kodak Co | Nouveaux composés azoïques, leur préparation et leurs applications |
| US2827451A (en) * | 1955-08-12 | 1958-03-18 | Eastman Kodak Co | 2-aminothiophene azo compounds |
| US2825726A (en) * | 1955-08-12 | 1958-03-04 | Eastman Kodak Co | Monoazo compounds containing a 2-aminothiophene nucleus |
| US2827450A (en) * | 1955-08-12 | 1958-03-18 | Eastman Kodak Co | 2-aminothiophene azo compounds |
| JPS4633226Y1 (enrdf_load_stackoverflow) * | 1968-05-07 | 1971-11-17 | ||
| FR2008404A1 (en) * | 1968-05-13 | 1970-01-23 | Eastman Kodak Co | Insoluble monoazo dyes for polyester fibres |
| GB1351381A (en) * | 1971-01-11 | 1974-04-24 | Ici Ltd | Disperse azo dyestuffs |
| GB1351382A (en) * | 1971-01-11 | 1974-04-24 | Ici Ltd | Disperse azo dyestuffs |
-
1972
- 1972-01-28 GB GB404672A patent/GB1394365A/en not_active Expired
-
1973
- 1973-01-18 CA CA161,746A patent/CA993865A/en not_active Expired
- 1973-01-18 CA CA161,747A patent/CA993866A/en not_active Expired
- 1973-01-18 CA CA161,748A patent/CA993867A/en not_active Expired
- 1973-01-23 BE BE794415D patent/BE794415A/xx not_active IP Right Cessation
- 1973-01-23 BE BE794416D patent/BE794416A/xx not_active IP Right Cessation
- 1973-01-23 BE BE794417D patent/BE794417A/xx not_active IP Right Cessation
- 1973-01-24 IT IT1954673A patent/IT983418B/it active
- 1973-01-24 IT IT1954773A patent/IT983419B/it active
- 1973-01-24 IT IT1954573A patent/IT983417B/it active
- 1973-01-25 NL NL7301078A patent/NL7301078A/xx not_active Application Discontinuation
- 1973-01-25 NL NL7301076A patent/NL7301076A/xx not_active Application Discontinuation
- 1973-01-25 NL NL7301081A patent/NL173656C/xx not_active IP Right Cessation
- 1973-01-25 NL NL7301077A patent/NL178083C/xx not_active IP Right Cessation
- 1973-01-26 CH CH118273A patent/CH569057A5/xx not_active IP Right Cessation
- 1973-01-26 FR FR7302873A patent/FR2169346B1/fr not_active Expired
- 1973-01-26 BR BR64373A patent/BR7300643D0/pt unknown
- 1973-01-26 FR FR7302870A patent/FR2169343B1/fr not_active Expired
- 1973-01-26 CH CH118573A patent/CH575409A5/xx not_active IP Right Cessation
- 1973-01-26 FR FR7302872A patent/FR2169345B1/fr not_active Expired
- 1973-01-26 BR BR64173A patent/BR7300641D0/pt unknown
- 1973-01-26 BR BR63773A patent/BR7300637D0/pt unknown
- 1973-01-26 CH CH118373A patent/CH572079A5/xx not_active IP Right Cessation
- 1973-01-26 FR FR7302871A patent/FR2169344B1/fr not_active Expired
- 1973-01-26 CH CH118473A patent/CH572080A5/xx not_active IP Right Cessation
- 1973-01-27 ES ES411050A patent/ES411050A1/es not_active Expired
- 1973-01-27 ES ES411052A patent/ES411052A1/es not_active Expired
- 1973-01-27 ES ES411049A patent/ES411049A1/es not_active Expired
- 1973-01-27 ES ES411051A patent/ES411051A1/es not_active Expired
- 1973-01-29 DE DE19732304201 patent/DE2304201C2/de not_active Expired
- 1973-01-29 JP JP1179573A patent/JPS5532740B2/ja not_active Expired
- 1973-01-29 DE DE19732304202 patent/DE2304202C2/de not_active Expired
- 1973-01-29 DE DE19732304218 patent/DE2304218C2/de not_active Expired
- 1973-01-29 JP JP1179673A patent/JPS5640177B2/ja not_active Expired
- 1973-01-29 JP JP1179773A patent/JPS5518710B2/ja not_active Expired
- 1973-01-29 JP JP1179473A patent/JPS5747214B2/ja not_active Expired
- 1973-01-29 DE DE19732304203 patent/DE2304203C2/de not_active Expired
- 1973-04-23 BE BE794418A patent/BE794418A/xx not_active IP Right Cessation
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2304201C2 (de) | 2-Aminothiophene | |
| DE2329722C2 (de) | Verfahren zur Herstellung von gegebenenfalls in 4-Stellung substituierten 2-Amino-3,5-dinitrothiophenen | |
| DE2162324C2 (de) | Verfahren zur Herstellung von 2-Mercapto-1,3,4-thiadiazolen | |
| DE1057124B (de) | Verfahren zur Herstellung von Sydnonen | |
| DE2330241C3 (de) | Chlorthio-N-phthalimid, Verfahren zu seiner Herstellung und seine Verwendung | |
| DE2640616A1 (de) | Verfahren zur herstellung von n-acylierten glycinderivaten, die durch aromatische reste alpha-substituiert sind, und die dabei erhaltenen produkte | |
| DE2326308A1 (de) | Verfahren zur herstellung von tetramisol | |
| DE1942454A1 (de) | Herstellung von Cephalosporinverbindungen | |
| CH432542A (de) | Verfahren zur Herstellung neuer Hydrazide | |
| DE2117050C3 (de) | Verfahren zur Herstellung von 1-(5-Nitrothiazol-2-yl)-2-oxotetrahydroimidazol | |
| DE2065879A1 (de) | Verfahren zur herstellung von dl-6- aminoacylamidopenicillansaeuren | |
| DE940588C (de) | Verfahren zur Herstellung von Chlorameisensaeureiminoestern | |
| CH459243A (de) | Verfahren zur Herstellung von neuen Lysergalen | |
| DE2340409A1 (de) | 1h-tetrazol-1-essigsaeure und deren ester, sowie verfahren zu deren herstellung | |
| AT204561B (de) | Verfahren zur Herstellung von neuen Phenazinderivaten | |
| DE947970C (de) | Verfahren zur Herstellung von 2, 5-Diphenyl-thiodiazol-(1,3,4) und seinen im Phenylrest substituierten Abkoemmlingen | |
| DE723051C (de) | Verfahren zur Herstellung von Dialkylmalonamidsaeureestern | |
| DE870113C (de) | Verfahren zur Herstellung von Amiden bzw. substituierten Amiden von Aminosaeuren oder Peptiden | |
| EP0102520A1 (de) | Verfahren zur Umkehrung der Konfiguration optisch aktiver Verbindungen und optisch aktive Zwischenprodukte dieses Verfahrens | |
| DE1793594C3 (de) | Verfahren zur Herstellung von substituierten Acrylnitrilen | |
| AT238170B (de) | Verfahren zur Herstellung von N-(2,3-Dimethylphenyl)-anthranilsäure und deren Salzen | |
| DE3013545A1 (de) | Heterocyclische thiomethylierung in der 3-position von 7-aminocephalosporansaeuren | |
| DE843727C (de) | Verfahren zur Herstellung von Leukoschwefelsaeureestern verkuepbarer Verbindungen der Anthrachinon- und Indigoreihe | |
| DE1963749C3 (de) | Verfahren zur Herstellung von l-(5-Nitro-2-thiazolyl)-2-oxo-tetrahydroiinidazol | |
| AT200129B (de) | Verfahren zur Herstellung von am Stickstoff ß-trinitroäthylsubstituierten Säureamiden |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OD | Request for examination | ||
| D2 | Grant after examination |