DE3015121C2 - - Google Patents
Info
- Publication number
- DE3015121C2 DE3015121C2 DE3015121A DE3015121A DE3015121C2 DE 3015121 C2 DE3015121 C2 DE 3015121C2 DE 3015121 A DE3015121 A DE 3015121A DE 3015121 A DE3015121 A DE 3015121A DE 3015121 C2 DE3015121 C2 DE 3015121C2
- Authority
- DE
- Germany
- Prior art keywords
- formula
- chloro
- alkoxy
- group
- carbonyl
- 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 - Lifetime
Links
- 150000001875 compounds Chemical class 0.000 claims description 15
- QQVDYSUDFZZPSU-UHFFFAOYSA-M chloromethylidene(dimethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)=CCl QQVDYSUDFZZPSU-UHFFFAOYSA-M 0.000 claims description 6
- 239000000975 dye Substances 0.000 claims description 6
- KJRBYUWRYRRPKN-UHFFFAOYSA-N 2-amino-4-chloro-1,3-thiazole-5-carbaldehyde Chemical compound NC1=NC(Cl)=C(C=O)S1 KJRBYUWRYRRPKN-UHFFFAOYSA-N 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 5
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 4
- 239000000543 intermediate Substances 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- HYMJHROUVPWYNQ-UHFFFAOYSA-N 2-amino-1,3-thiazol-4-one Chemical compound NC1=NC(=O)CS1 HYMJHROUVPWYNQ-UHFFFAOYSA-N 0.000 claims description 3
- 239000003929 acidic solution Substances 0.000 claims description 3
- 239000007795 chemical reaction product Substances 0.000 claims description 3
- -1 cyclohexyloxycarbonyl Chemical group 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 6
- 239000000243 solution Substances 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical class NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 3
- 239000000987 azo dye Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- DYZMXGCHWXQLCM-UHFFFAOYSA-N 2-[(2-amino-4-chloro-1,3-thiazol-5-yl)methylidene]propanedinitrile Chemical compound NC=1SC(=C(N=1)Cl)C=C(C#N)C#N DYZMXGCHWXQLCM-UHFFFAOYSA-N 0.000 description 2
- GJTWEAFBOIYNLZ-UHFFFAOYSA-N 4-chloro-1,3-thiazole-5-carbaldehyde Chemical class ClC=1N=CSC=1C=O GJTWEAFBOIYNLZ-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 2
- CUONGYYJJVDODC-UHFFFAOYSA-N malononitrile Chemical compound N#CCC#N CUONGYYJJVDODC-UHFFFAOYSA-N 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- FEWLNYSYJNLUOO-UHFFFAOYSA-N 1-Piperidinecarboxaldehyde Chemical compound O=CN1CCCCC1 FEWLNYSYJNLUOO-UHFFFAOYSA-N 0.000 description 1
- 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 1
- YBDFGIGPQKUYGW-UHFFFAOYSA-N 2-amino-1,3-thiazol-3-ium-4-one;chloride Chemical compound Cl.NC1=NC(=O)CS1 YBDFGIGPQKUYGW-UHFFFAOYSA-N 0.000 description 1
- 229920002284 Cellulose triacetate Polymers 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
- NNLVGZFZQQXQNW-ADJNRHBOSA-N [(2r,3r,4s,5r,6s)-4,5-diacetyloxy-3-[(2s,3r,4s,5r,6r)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6s)-4,5,6-triacetyloxy-2-(acetyloxymethyl)oxan-3-yl]oxyoxan-2-yl]methyl acetate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](OC(C)=O)[C@H]1OC(C)=O)O[C@H]1[C@@H]([C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](COC(C)=O)O1)OC(C)=O)COC(=O)C)[C@@H]1[C@@H](COC(C)=O)O[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O NNLVGZFZQQXQNW-ADJNRHBOSA-N 0.000 description 1
- VJMAITQRABEEKP-UHFFFAOYSA-N [6-(phenylmethoxymethyl)-1,4-dioxan-2-yl]methyl acetate Chemical compound O1C(COC(=O)C)COCC1COCC1=CC=CC=C1 VJMAITQRABEEKP-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 238000004140 cleaning Methods 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
- 239000000986 disperse dye Substances 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 235000015243 ice cream Nutrition 0.000 description 1
- 125000001841 imino group Chemical group [H]N=* 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- AJDUTMFFZHIJEM-UHFFFAOYSA-N n-(9,10-dioxoanthracen-1-yl)-4-[4-[[4-[4-[(9,10-dioxoanthracen-1-yl)carbamoyl]phenyl]phenyl]diazenyl]phenyl]benzamide Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2NC(=O)C(C=C1)=CC=C1C(C=C1)=CC=C1N=NC(C=C1)=CC=C1C(C=C1)=CC=C1C(=O)NC1=CC=CC2=C1C(=O)C1=CC=CC=C1C2=O AJDUTMFFZHIJEM-UHFFFAOYSA-N 0.000 description 1
- JIKUXBYRTXDNIY-UHFFFAOYSA-N n-methyl-n-phenylformamide Chemical compound O=CN(C)C1=CC=CC=C1 JIKUXBYRTXDNIY-UHFFFAOYSA-N 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000001043 yellow dye 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
- C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
- C09B23/0091—Methine or polymethine dyes, e.g. cyanine dyes having only one heterocyclic ring at one end of the methine chain, e.g. hemicyamines, hemioxonol
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
- C07D277/38—Nitrogen atoms
- C07D277/40—Unsubstituted amino or imino radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
- C07D277/38—Nitrogen atoms
- C07D277/42—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
- C07D277/56—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH414279A CH644369A5 (de) | 1979-05-03 | 1979-05-03 | 2-amino-4-chlorthiazolverbindungen. |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE3015121A1 DE3015121A1 (de) | 1980-11-13 |
| DE3015121C2 true DE3015121C2 (en, 2012) | 1992-02-27 |
Family
ID=4270600
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19803015121 Granted DE3015121A1 (de) | 1979-05-03 | 1980-04-19 | 4-halogen-5-formylthiazolverbindungen |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US4395544A (en, 2012) |
| JP (1) | JPS55147558A (en, 2012) |
| BR (1) | BR8002694A (en, 2012) |
| CH (1) | CH644369A5 (en, 2012) |
| DE (1) | DE3015121A1 (en, 2012) |
| ES (1) | ES491139A0 (en, 2012) |
| FR (1) | FR2455591A1 (en, 2012) |
| GB (1) | GB2056969B (en, 2012) |
| IT (1) | IT1128154B (en, 2012) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3303704A1 (de) * | 1983-02-04 | 1984-08-09 | Bayer Ag, 5090 Leverkusen | 2,4-dichlor-5-thiazolcarboxaldehyd und ein verfahren zu seiner herstellung |
| CH664762A5 (de) * | 1984-08-30 | 1988-03-31 | Sandoz Ag | Thiophen-azofarbstoffe. |
| JPH02113070A (ja) * | 1988-10-20 | 1990-04-25 | Fuji Photo Film Co Ltd | 色素 |
| DE4010514A1 (de) * | 1990-04-02 | 1991-10-10 | Basf Ag | Verfahren zur herstellung von 2-amino-5-formyl-4-halogenthiazolen |
| DE4120362A1 (de) * | 1991-06-20 | 1992-12-24 | Basf Ag | Thiazolazofarbstoffe mit einer kupplungskomponente aus der diphenylaminreihe |
| DE4215495A1 (de) * | 1992-05-12 | 1993-11-18 | Basf Ag | Azofarbstoffe mit einer acetalisierten Diazokomponente aus der Thiophen- oder Thiazolreihe |
| EP0578870B1 (en) * | 1992-07-14 | 1996-12-11 | Agfa-Gevaert N.V. | Thiazolylazoaniline dyes for use in thermal dye sublimation transfer |
| US5356857A (en) * | 1993-05-17 | 1994-10-18 | Agfa-Gevaert, N.V. | Triazene dyes for use in thermal transfer printing |
| DE4401912A1 (de) * | 1994-01-24 | 1995-07-27 | Basf Ag | Methinfarbstoffe in der nichtlinearen Optik |
| EP0687674A1 (en) * | 1994-06-17 | 1995-12-20 | Agfa-Gevaert N.V. | Preparation of 2-amino-4-alkoxythiazoles being negatively substituted in the 5 position |
Family Cites Families (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1137024B (de) * | 1962-09-27 | Bayer Ag | Verfahren zur Herstellung von substituierten 2-Aminothiazol-(5)-aldehyden | |
| FR925954A (fr) * | 1946-04-05 | 1947-09-18 | Applic Therapeutiques Therapli | Composés thiazoliques chlorés et leur procédé de préparation |
| FR1006623A (fr) * | 1947-02-24 | 1952-04-25 | Applic Therapeutiques Soc Gen | Nouveau produit chimique, utilisable comme hypnotique, et son procédé de préparation |
| DE1182234B (de) * | 1962-11-08 | 1964-11-26 | Bayer Ag | Verfahren zur Herstellung von Thiazol-5-aldehyden |
| FR1533184A (fr) * | 1965-04-06 | 1968-07-19 | Pechiney Saint Gobain | Dérivés du thiazole |
| US3547917A (en) * | 1966-12-07 | 1970-12-15 | Uniroyal Inc | 2-amino-4-methylthiazole-5-carboxamides |
| US3444178A (en) * | 1967-06-16 | 1969-05-13 | Monsanto Co | Certain halogenated 2-(2-thiazolyl) aminofuran-5-ones |
| US3573289A (en) * | 1967-10-27 | 1971-03-30 | Eastman Kodak Co | Cationic methine compounds |
| US3829410A (en) * | 1970-03-19 | 1974-08-13 | Eastman Kodak Co | 5-(cyanovinylene)-2-thiazolylazoaniline compounds |
| JPS5537555B2 (en, 2012) * | 1973-10-24 | 1980-09-29 | ||
| CH622541A5 (en, 2012) | 1976-07-12 | 1981-04-15 | Sandoz Ag | |
| NO781300L (no) * | 1977-04-20 | 1978-10-23 | Ici Ltd | Fremgangsmaate for fremstilling av fysiologisk aktive guanidinderivater |
| US4165378A (en) * | 1977-04-20 | 1979-08-21 | Ici Americas Inc. | Guanidine derivatives of imidazoles and thiazoles |
| GB1583377A (en) | 1977-04-25 | 1981-01-28 | Ici Ltd | Disperse azo dyestuffs derived from a 2-aminothiophene-5-aldehyde |
| DE2837121A1 (de) * | 1977-09-05 | 1979-03-15 | Sandoz Ag | Organische verbindungen |
| DE2805177A1 (de) * | 1978-02-08 | 1979-08-09 | Sandoz Ag | Azo-dispersionsfarbstoffe, ihre herstellung und verwendung |
| DD136147A1 (de) * | 1978-04-28 | 1979-06-20 | Harald Niegel | Verfahren zur herstellung von methin-dispersionsfarbstoffen |
-
1979
- 1979-05-03 CH CH414279A patent/CH644369A5/de not_active IP Right Cessation
-
1980
- 1980-04-19 DE DE19803015121 patent/DE3015121A1/de active Granted
- 1980-04-29 GB GB8014035A patent/GB2056969B/en not_active Expired
- 1980-04-29 FR FR8009618A patent/FR2455591A1/fr active Granted
- 1980-04-30 IT IT48560/80A patent/IT1128154B/it active
- 1980-04-30 BR BR8002694A patent/BR8002694A/pt unknown
- 1980-05-01 JP JP5716380A patent/JPS55147558A/ja active Granted
- 1980-05-02 ES ES491139A patent/ES491139A0/es active Granted
-
1981
- 1981-05-15 US US06/264,019 patent/US4395544A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| GB2056969A (en) | 1981-03-25 |
| IT8048560A0 (it) | 1980-04-30 |
| JPS55147558A (en) | 1980-11-17 |
| JPH0248554B2 (en, 2012) | 1990-10-25 |
| GB2056969B (en) | 1983-12-07 |
| CH644369A5 (de) | 1984-07-31 |
| ES8104261A1 (es) | 1981-04-16 |
| FR2455591A1 (fr) | 1980-11-28 |
| DE3015121A1 (de) | 1980-11-13 |
| ES491139A0 (es) | 1981-04-16 |
| FR2455591B1 (en, 2012) | 1983-05-20 |
| BR8002694A (pt) | 1980-12-16 |
| IT1128154B (it) | 1986-05-28 |
| US4395544A (en) | 1983-07-26 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8327 | Change in the person/name/address of the patent owner |
Owner name: BASF AG, 67063 LUDWIGSHAFEN, DE |
|
| 8339 | Ceased/non-payment of the annual fee | ||
| 8370 | Indication of lapse of patent is to be deleted |