DE2643640A1 - 3-trifluormethyl-4-aryl-5-amino- pyrazole, verfahren zu ihrer herstellung und deren verwendung als diazotierbare basen fuer die herstellung von farbstoffen - Google Patents
3-trifluormethyl-4-aryl-5-amino- pyrazole, verfahren zu ihrer herstellung und deren verwendung als diazotierbare basen fuer die herstellung von farbstoffenInfo
- Publication number
- DE2643640A1 DE2643640A1 DE19762643640 DE2643640A DE2643640A1 DE 2643640 A1 DE2643640 A1 DE 2643640A1 DE 19762643640 DE19762643640 DE 19762643640 DE 2643640 A DE2643640 A DE 2643640A DE 2643640 A1 DE2643640 A1 DE 2643640A1
- Authority
- DE
- Germany
- Prior art keywords
- production
- trifluoromethyl
- general formula
- dyes
- aryl
- 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.)
- Withdrawn
Links
- 238000000034 method Methods 0.000 title claims description 9
- 238000004519 manufacturing process Methods 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims description 10
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 239000000975 dye Substances 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 230000015572 biosynthetic process Effects 0.000 claims description 2
- 230000008878 coupling Effects 0.000 claims description 2
- 238000010168 coupling process Methods 0.000 claims description 2
- 238000005859 coupling reaction Methods 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=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 description 2
- 238000003786 synthesis reaction Methods 0.000 claims description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 239000000203 mixture Substances 0.000 description 4
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- -1 Benzene hydrocarbon Chemical class 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 3
- BLFCSOQPFPFQHF-UHFFFAOYSA-N 4,4,4-trifluoro-3-oxo-2-phenylbutanenitrile Chemical compound FC(F)(F)C(=O)C(C#N)C1=CC=CC=C1 BLFCSOQPFPFQHF-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 239000007822 coupling agent Substances 0.000 description 2
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 2
- 238000004043 dyeing Methods 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- CIPVVROJHKLHJI-UHFFFAOYSA-N n,n-diethyl-3-methylaniline Chemical compound CCN(CC)C1=CC=CC(C)=C1 CIPVVROJHKLHJI-UHFFFAOYSA-N 0.000 description 2
- 229920002239 polyacrylonitrile Polymers 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- SFWZZSXCWQTORH-UHFFFAOYSA-N 1-methyl-2-phenylindole Chemical compound C=1C2=CC=CC=C2N(C)C=1C1=CC=CC=C1 SFWZZSXCWQTORH-UHFFFAOYSA-N 0.000 description 1
- JVVRJMXHNUAPHW-UHFFFAOYSA-N 1h-pyrazol-5-amine Chemical compound NC=1C=CNN=1 JVVRJMXHNUAPHW-UHFFFAOYSA-N 0.000 description 1
- XXJMDOIBGIZHNR-UHFFFAOYSA-N 2,5-diethoxy-n,n-diethylaniline Chemical compound CCOC1=CC=C(OCC)C(N(CC)CC)=C1 XXJMDOIBGIZHNR-UHFFFAOYSA-N 0.000 description 1
- VUUHXRVVDUAGOL-UHFFFAOYSA-N 3-(3-methylanilino)propanenitrile Chemical compound CC1=CC=CC(NCCC#N)=C1 VUUHXRVVDUAGOL-UHFFFAOYSA-N 0.000 description 1
- WYRNRZQRKCXPLA-UHFFFAOYSA-N 3-(n-ethylanilino)propanenitrile Chemical compound N#CCCN(CC)C1=CC=CC=C1 WYRNRZQRKCXPLA-UHFFFAOYSA-N 0.000 description 1
- CHHRQHHCHIPUPH-UHFFFAOYSA-N 4-[[1,2-dimethyl-4-phenyl-5-(trifluoromethyl)pyrazol-2-ium-3-yl]diazenyl]-N,N-diethyl-3-methylaniline Chemical compound C[N+]=1N(C(=C(C1N=NC1=C(C=C(C=C1)N(CC)CC)C)C1=CC=CC=C1)C(F)(F)F)C CHHRQHHCHIPUPH-UHFFFAOYSA-N 0.000 description 1
- 229920002972 Acrylic fiber Polymers 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 229910004379 HoF 3 Inorganic materials 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 125000002843 carboxylic acid group Chemical group 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 1
- RAXZICBKEQDBNQ-UHFFFAOYSA-N n,n,2,5-tetramethylaniline Chemical compound CN(C)C1=CC(C)=CC=C1C RAXZICBKEQDBNQ-UHFFFAOYSA-N 0.000 description 1
- QFXHTZHSMUOIPN-UHFFFAOYSA-N n,n,n'-triethyl-n'-(3-methylphenyl)ethane-1,2-diamine Chemical compound CCN(CC)CCN(CC)C1=CC=CC(C)=C1 QFXHTZHSMUOIPN-UHFFFAOYSA-N 0.000 description 1
- KGFAREHEJGDILZ-UHFFFAOYSA-N n,n-diethyl-3-methoxyaniline Chemical compound CCN(CC)C1=CC=CC(OC)=C1 KGFAREHEJGDILZ-UHFFFAOYSA-N 0.000 description 1
- LNSFUEPYYQXLFN-UHFFFAOYSA-N n-ethyl-3-methyl-n-(2,2,2-trifluoroethyl)aniline Chemical compound FC(F)(F)CN(CC)C1=CC=CC(C)=C1 LNSFUEPYYQXLFN-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical compound O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole 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
- C07D231/38—Nitrogen atoms
-
- 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
- C09B29/0029—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds the heterocyclic ring containing only nitrogen as heteroatom
- C09B29/0037—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds the heterocyclic ring containing only nitrogen as heteroatom containing a five-membered heterocyclic ring with two nitrogen atoms
-
- 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
- C09B44/00—Azo dyes containing onium groups
- C09B44/10—Azo dyes containing onium groups containing cyclammonium groups attached to an azo group by a carbon atom of the ring system
- C09B44/14—1,2-Diazoles or hydrogenated 1,2-diazoles ; Pyrazolium; Indazolium
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7529873A FR2326421A1 (fr) | 1975-09-30 | 1975-09-30 | Nouveaux trifluoromethyl-3-aryl-4 amino-5 pyrazoles et leur application comme bases diazotables pour la synthese de matieres colorantes |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2643640A1 true DE2643640A1 (de) | 1977-04-07 |
Family
ID=9160632
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19762643640 Withdrawn DE2643640A1 (de) | 1975-09-30 | 1976-09-28 | 3-trifluormethyl-4-aryl-5-amino- pyrazole, verfahren zu ihrer herstellung und deren verwendung als diazotierbare basen fuer die herstellung von farbstoffen |
Country Status (6)
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5616723A (en) * | 1993-05-05 | 1997-04-01 | H uls Aktiengesellschaft | Process for the preparation of 3-amino-5-methylpyrazole |
| EP0846686A1 (en) * | 1996-11-30 | 1998-06-10 | Pfizer Limited | 1-Phenyl-pyrazol derivatives and their use as parasiticidal agents |
| US6069157A (en) * | 1997-11-25 | 2000-05-30 | Pfizer Inc. | Parasiticidal compounds |
| EP2266973A1 (de) | 2009-05-29 | 2010-12-29 | Bayer CropScience AG | Pyrazinylpyrazole |
| EP2275422A1 (de) | 2006-12-20 | 2011-01-19 | Bayer CropScience AG | Pyrimidinylpyrazole als insektizide und parasitizide Wirkstoffe |
| EP2374791A1 (de) | 2008-08-14 | 2011-10-12 | Bayer CropScience Aktiengesellschaft | Insektizide 4-Phenyl-1H-pyrazole |
-
1975
- 1975-09-30 FR FR7529873A patent/FR2326421A1/fr active Granted
-
1976
- 1976-09-28 NL NL7610716A patent/NL7610716A/xx not_active Application Discontinuation
- 1976-09-28 DE DE19762643640 patent/DE2643640A1/de not_active Withdrawn
- 1976-09-29 JP JP11705676A patent/JPS5242521A/ja active Pending
- 1976-09-29 BE BE171068A patent/BE846732A/xx unknown
- 1976-09-29 GB GB4034976A patent/GB1514862A/en not_active Expired
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5616723A (en) * | 1993-05-05 | 1997-04-01 | H uls Aktiengesellschaft | Process for the preparation of 3-amino-5-methylpyrazole |
| EP0846686A1 (en) * | 1996-11-30 | 1998-06-10 | Pfizer Limited | 1-Phenyl-pyrazol derivatives and their use as parasiticidal agents |
| US6156782A (en) * | 1996-11-30 | 2000-12-05 | Pfizer Inc | Parasiticidal compounds |
| US6069157A (en) * | 1997-11-25 | 2000-05-30 | Pfizer Inc. | Parasiticidal compounds |
| EP2275422A1 (de) | 2006-12-20 | 2011-01-19 | Bayer CropScience AG | Pyrimidinylpyrazole als insektizide und parasitizide Wirkstoffe |
| EP2374791A1 (de) | 2008-08-14 | 2011-10-12 | Bayer CropScience Aktiengesellschaft | Insektizide 4-Phenyl-1H-pyrazole |
| EP2266973A1 (de) | 2009-05-29 | 2010-12-29 | Bayer CropScience AG | Pyrazinylpyrazole |
| US8513260B2 (en) | 2009-05-29 | 2013-08-20 | Bayer Cropscience Ag | Pyrazinylpyrazoles |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2326421A1 (fr) | 1977-04-29 |
| NL7610716A (nl) | 1977-04-01 |
| FR2326421B1 (US08177716-20120515-C00003.png) | 1979-04-06 |
| GB1514862A (en) | 1978-06-21 |
| BE846732A (US08177716-20120515-C00003.png) | 1977-03-29 |
| JPS5242521A (en) | 1977-04-02 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OGA | New person/name/address of the applicant | ||
| 8139 | Disposal/non-payment of the annual fee |