GB797144A - Improvements in or relating to pyrazole compounds - Google Patents
Improvements in or relating to pyrazole compoundsInfo
- Publication number
- GB797144A GB797144A GB3269555A GB3269555A GB797144A GB 797144 A GB797144 A GB 797144A GB 3269555 A GB3269555 A GB 3269555A GB 3269555 A GB3269555 A GB 3269555A GB 797144 A GB797144 A GB 797144A
- Authority
- GB
- United Kingdom
- Prior art keywords
- methyl
- prepared
- pyrazole
- phenyl
- alkyl
- 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
- 150000003217 pyrazoles Chemical class 0.000 title abstract 2
- -1 1:3-diphenylpyrazole Chemical compound 0.000 abstract 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N acetic acid anhydride Natural products CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 abstract 4
- 125000000217 alkyl group Chemical group 0.000 abstract 4
- 125000003118 aryl group Chemical group 0.000 abstract 3
- CLGKHQCZJWOXGO-UHFFFAOYSA-N 1-(4-chlorophenyl)pyrazole Chemical compound C1=CC(Cl)=CC=C1N1N=CC=C1 CLGKHQCZJWOXGO-UHFFFAOYSA-N 0.000 abstract 2
- LRGBDJBDJXZTTD-UHFFFAOYSA-N 1h-pyrazole-4-carbaldehyde Chemical class O=CC=1C=NNC=1 LRGBDJBDJXZTTD-UHFFFAOYSA-N 0.000 abstract 2
- RJXLUGSJEMSDPK-UHFFFAOYSA-N 3-methyl-1-phenylpyrazole Chemical compound N1=C(C)C=CN1C1=CC=CC=C1 RJXLUGSJEMSDPK-UHFFFAOYSA-N 0.000 abstract 2
- XXNOGQJZAOXWAQ-UHFFFAOYSA-N 4-chlorophenylhydrazine Chemical compound NNC1=CC=C(Cl)C=C1 XXNOGQJZAOXWAQ-UHFFFAOYSA-N 0.000 abstract 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 abstract 2
- 125000003545 alkoxy group Chemical group 0.000 abstract 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 abstract 2
- 239000000975 dye Substances 0.000 abstract 2
- 229910052736 halogen Inorganic materials 0.000 abstract 2
- 150000002367 halogens Chemical group 0.000 abstract 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 abstract 2
- QGKMIGUHVLGJBR-UHFFFAOYSA-M (4z)-1-(3-methylbutyl)-4-[[1-(3-methylbutyl)quinolin-1-ium-4-yl]methylidene]quinoline;iodide Chemical compound [I-].C12=CC=CC=C2N(CCC(C)C)C=CC1=CC1=CC=[N+](CCC(C)C)C2=CC=CC=C12 QGKMIGUHVLGJBR-UHFFFAOYSA-M 0.000 abstract 1
- XHTYQFMRBQUCPX-UHFFFAOYSA-N 1,1,3,3-tetramethoxypropane Chemical compound COC(OC)CC(OC)OC XHTYQFMRBQUCPX-UHFFFAOYSA-N 0.000 abstract 1
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 abstract 1
- HATADCJHNNRIJY-UHFFFAOYSA-N 1-(4-methoxyphenyl)pyrazole Chemical compound C1=CC(OC)=CC=C1N1N=CC=C1 HATADCJHNNRIJY-UHFFFAOYSA-N 0.000 abstract 1
- WITMXBRCQWOZPX-UHFFFAOYSA-N 1-phenylpyrazole Chemical compound C1=CC=NN1C1=CC=CC=C1 WITMXBRCQWOZPX-UHFFFAOYSA-N 0.000 abstract 1
- MCGBIXXDQFWVDW-UHFFFAOYSA-N 4,5-dihydro-1h-pyrazole Chemical compound C1CC=NN1 MCGBIXXDQFWVDW-UHFFFAOYSA-N 0.000 abstract 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 abstract 1
- YTSFYTDPSSFCLU-UHFFFAOYSA-N 5-chloro-1,3-benzothiazole Chemical compound ClC1=CC=C2SC=NC2=C1 YTSFYTDPSSFCLU-UHFFFAOYSA-N 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 125000002252 acyl group Chemical group 0.000 abstract 1
- 125000004442 acylamino group Chemical group 0.000 abstract 1
- 150000001450 anions Chemical group 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- 239000007795 chemical reaction product Substances 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- QELUYTUMUWHWMC-UHFFFAOYSA-N edaravone Chemical compound O=C1CC(C)=NN1C1=CC=CC=C1 QELUYTUMUWHWMC-UHFFFAOYSA-N 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- JIKUXBYRTXDNIY-UHFFFAOYSA-N n-methyl-n-phenylformamide Chemical compound O=CN(C)C1=CC=CC=C1 JIKUXBYRTXDNIY-UHFFFAOYSA-N 0.000 abstract 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 238000010992 reflux Methods 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 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
- C09B23/10—The polymethine chain containing an even number of >CH- groups
- C09B23/105—The polymethine chain containing an even number of >CH- groups two >CH- 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
- C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
- C09B23/02—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups
- C09B23/04—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups one >CH- group, e.g. cyanines, isocyanines, pseudocyanines
Abstract
Pyrazole-4-aldehydes of the general formula <FORM:0797144/IV (b)/1> wherein R1 is an aryl group which may be substituted with halogen, alkoxy or acylamino groups, and R2 and R3 are hydrogen or alkyl or aryl groups, are prepared by reacting pyrazoles of the formula <FORM:0797144/IV (b)/2> with N-methyl formanilide and phosphorus oxychloride and decomposing the reaction product with water. Examples are given of the preparation of the 4-aldehydes from 1-phenyl-3:5-dimethylpyrazole, 1-phenylpyrazole, 1:3-diphenylpyrazole, 1-p-chlorophenylpyrazole, 1-(21:51 - dichlorophenyl) - pyrazole, 1 - p - methoxyphenylpyrazole, 3 - methyl - 1 - phenylpyrazole and 1-p-chlorophenyl-3:5-dimethylpyrazole. 1 - p - Chlorophenyl - 3:5 - dimethylpyrazole is prepared by reacting acetylacetone with p-chlorophenylhydrazine. 1-p-Chlorophenylpyrazole is prepared by refluxing p-chlorophenylhydrazine with malondialdehyde-tetramethyl acetal in ethanol while adding conc. HCl. 1-(21:51-Dichlorophenyl)-pyrazole and 1-p-methoxyphenyl-pyrazole were prepared in an analogous manner. 3-Methyl-1-phenylpyrazole is prepared by heating 3-methyl-1-phenyl- D 2-pyrazoline with acetic acid and acetic anhydride and adding red lead. 1:3-Diphenyl-pyrazole is similarly prepared.ALSO:Cyanine dyes of the general formula <FORM:0797144/IV (b)/1> or <FORM:0797144/IV (b)/2> wherein R1 is an acyl group which may carry halogen, alkoxy or acylamino substituents, R2 and R3 are H, alkyl or aryl, R4 is alkyl, X is an anion and D1 and D2 complete 5- or 6-membered nuclei, are prepared by reacting a pyrazole-4-aldehyde with a quaternary cyclammonium compound having a reactive 2-methyl group, or with a cyclic ketomethylene compound. In the examples, R1 is phenyl, p-chlorophenyl, 2 : 5-dichlorophenyl, or p-methoxyphenyl, R2 or R3 is H, methyl or phenyl, D1 completes a benzthiazole, 5-chlorobenzthiazole, 6 : 7-benz-benzthiazole, benzoxazole, 3 : 3-dimethylindolene or 2-quinoline nucleus and D2 completes a 3-methyl - 1 - phenyl - 5 - pyrazolone or 3 - ethyl-2 - thio - thiazolid - 4 - one nucleus. According to the Provisional Specification, the dyes of the first formula may be ones wherein R1, R2 and R3 also are aralkyl groups or R1 is an alkyl group, or the nucleus D1 may be the residue of a quarternary salt having a reactive methyl group in the 4-position.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3269555A GB797144A (en) | 1955-11-15 | 1955-11-15 | Improvements in or relating to pyrazole compounds |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3269555A GB797144A (en) | 1955-11-15 | 1955-11-15 | Improvements in or relating to pyrazole compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB797144A true GB797144A (en) | 1958-06-25 |
Family
ID=10342625
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3269555A Expired GB797144A (en) | 1955-11-15 | 1955-11-15 | Improvements in or relating to pyrazole compounds |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB797144A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3073820A (en) * | 1960-08-10 | 1963-01-15 | Arnold F Plue | 2-pyrazolinyl-vinyl-1, 3, 3 trimethyl indolenines |
| US3515722A (en) * | 1966-03-11 | 1970-06-02 | Eastman Kodak Co | Cyanine dyes |
| US3542772A (en) * | 1966-03-11 | 1970-11-24 | Eastman Kodak Co | Cyanine dyes containing a 1-heterocyclic substituted 4-pyrazolyl nucleus |
| US3974176A (en) | 1973-08-16 | 1976-08-10 | Byk-Gulden Lomberg Chemische Fabrik Gmbh | Halogen pyrazoles derivatives, a method for producing these halogen pyrazole derivatives and medicaments containing them |
-
1955
- 1955-11-15 GB GB3269555A patent/GB797144A/en not_active Expired
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3073820A (en) * | 1960-08-10 | 1963-01-15 | Arnold F Plue | 2-pyrazolinyl-vinyl-1, 3, 3 trimethyl indolenines |
| US3515722A (en) * | 1966-03-11 | 1970-06-02 | Eastman Kodak Co | Cyanine dyes |
| US3542772A (en) * | 1966-03-11 | 1970-11-24 | Eastman Kodak Co | Cyanine dyes containing a 1-heterocyclic substituted 4-pyrazolyl nucleus |
| US3974176A (en) | 1973-08-16 | 1976-08-10 | Byk-Gulden Lomberg Chemische Fabrik Gmbh | Halogen pyrazoles derivatives, a method for producing these halogen pyrazole derivatives and medicaments containing them |
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