GB813866A - New 1:3-di-substituted-5-pyrazolones and their use in colour photography - Google Patents
New 1:3-di-substituted-5-pyrazolones and their use in colour photographyInfo
- Publication number
- GB813866A GB813866A GB3824356A GB3824356A GB813866A GB 813866 A GB813866 A GB 813866A GB 3824356 A GB3824356 A GB 3824356A GB 3824356 A GB3824356 A GB 3824356A GB 813866 A GB813866 A GB 813866A
- Authority
- GB
- United Kingdom
- Prior art keywords
- benziminazolyl
- pyrazolone
- methyl
- alkyl
- group
- 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
- 229940051880 analgesics and antipyretics pyrazolones Drugs 0.000 title abstract 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 6
- 125000000217 alkyl group Chemical group 0.000 abstract 6
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine Substances NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 abstract 5
- 229910052739 hydrogen Inorganic materials 0.000 abstract 5
- 239000001257 hydrogen Substances 0.000 abstract 5
- 150000001875 compounds Chemical class 0.000 abstract 4
- NHLAPJMCARJFOG-UHFFFAOYSA-N 3-methyl-1,4-dihydropyrazol-5-one Chemical compound CC1=NNC(=O)C1 NHLAPJMCARJFOG-UHFFFAOYSA-N 0.000 abstract 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 3
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 3
- 125000003118 aryl group Chemical group 0.000 abstract 3
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical class O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 abstract 3
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 abstract 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 abstract 2
- 238000009835 boiling Methods 0.000 abstract 2
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 abstract 2
- 229940093858 ethyl acetoacetate Drugs 0.000 abstract 2
- 125000000623 heterocyclic group Chemical group 0.000 abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- -1 phenyl naphthyl Chemical group 0.000 abstract 2
- 239000002904 solvent Substances 0.000 abstract 2
- 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 abstract 1
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 abstract 1
- DGDVNWQOSVJPNR-UHFFFAOYSA-N 2-(furan-3-yl)-4H-pyrazol-3-one Chemical compound O1C=C(C=C1)N1N=CCC1=O DGDVNWQOSVJPNR-UHFFFAOYSA-N 0.000 abstract 1
- GKKZMYDNDDMXSE-UHFFFAOYSA-N Ethyl 3-oxo-3-phenylpropanoate Chemical compound CCOC(=O)CC(=O)C1=CC=CC=C1 GKKZMYDNDDMXSE-UHFFFAOYSA-N 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 1
- 125000002837 carbocyclic group Chemical group 0.000 abstract 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 125000002541 furyl group Chemical group 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 abstract 1
- 150000002431 hydrogen Chemical group 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 150000002790 naphthalenes Chemical class 0.000 abstract 1
- 125000004923 naphthylmethyl group Chemical group C1(=CC=CC2=CC=CC=C12)C* 0.000 abstract 1
- 230000020477 pH reduction Effects 0.000 abstract 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 1
- 238000010992 reflux Methods 0.000 abstract 1
- 229910000029 sodium carbonate Inorganic materials 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
Classifications
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
- G03C7/00—Multicolour photographic processes or agents therefor; Regeneration of such processing agents; Photosensitive materials for multicolour processes
- G03C7/30—Colour processes using colour-coupling substances; Materials therefor; Preparing or processing such materials
- G03C7/32—Colour coupling substances
- G03C7/36—Couplers containing compounds with active methylene groups
- G03C7/38—Couplers containing compounds with active methylene groups in rings
- G03C7/384—Couplers containing compounds with active methylene groups in rings in pyrazolone rings
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
The invention comprises benziminazolyl pyrazolones of the general formula <FORM:0813866/IV (b)/1> in which R1 represents an alkyl, aralkyl, aryl or heterocyclic group, e.g. methyl, ethyl, propyl, butyl, benzyl, naphthylmethyl, phenyl naphthyl or furyl and R2 represents hydrogen, a halogen, an alkyl or alkoxy group or other substituent. The compounds are colour couplers (see Group XX) and may be prepared by reacting a compound of the general formula R1COCH2COOR3 with a compound <FORM:0813866/IV (b)/2> R1 and R2 being as defined above and R3 representing hydrogen or an alkyl group. Reaction is preferably effected in a solvent medium with heating. In examples: (1) 2-hydrazino-benziminazole, prepared by refluxing 2-methylthiobenziminazole with hydrazine hydrate, is refluxed with ethyl acetoacetate in acetic acid, the solvent is thereafter removed and the residue heated with aqueous sodium carbonate and the resulting 1 - 21 - benziminazolyl - 3 - methyl - 5-pyrazolone recovered by acidification; (2) in like manner, 2-hydrazino-5-methylbenziminazole, prepared from 2-methylthio-5-benziminazole, yields 1 - (51 - methyl - 21 - benziminazolyl) 3 - methyl - 5 - pyrazolone; (3) 1 - (51-chloro - 21 - benziminazolyl) 3 - methyl - 5-pyrazolone is similarly obtained from 5-chloro2 - hydrazinobenziminazole; (4) 5 - ethoxy - 2-benziminazolyl-hydrazine obtained as in (1) from 2 - methylthio - 5 - ethyoxy benziminazole, yields 1 - (51 - ethoxy - 21 - benziminazolyl) 3 - methyl - 5 - pyrazolone; (5) the hydrazine used in (1) is reacted with ethyl aceto acetate in a boiling mixture of acetic acid and 2-methoxyethanol yielding the same benziminazolyl pyrazolone; (6) and (7), 2-benziminazolyl hydrazine is reacted in boiling 2-methoxy ethanol with ethyl benzoyl acetate or ethyl furoyl acetate yielding 1-21-benziminazolyl-3-phenyl- or 3-furyl-5-pyrazolone respectively. According to the Provisional Specification, new pyrazolones having the general formula <FORM:0813866/IV (b)/3> wherein R1 is an alkyl, aralkyl, aryl or hetero cyclic group, R2 is hydrogen or an alkyl, aralkyl or aryl group and R3 and R4 individually represent hydrogen or carbalkoxy, e.g. carbethoxy groups or together form part of a carbocyclic ring, e.g. a benzene or naphthalene nucleus, may be prepared by reacting together compounds of the general formula R1-CO-CH2 COOR5 and <FORM:0813866/IV (b)/4> wherein R5 is hydrogen or an alkyl group.
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB813866A true GB813866A (en) | 1959-05-27 |
Family
ID=1745211
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3824356A Expired GB813866A (en) | 1956-12-14 | New 1:3-di-substituted-5-pyrazolones and their use in colour photography |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB813866A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2013129674A1 (en) * | 2012-03-01 | 2013-09-06 | 学校法人兵庫医科大学 | Novel benzimidazole derivative and use thereof |
-
1956
- 1956-12-14 GB GB3824356A patent/GB813866A/en not_active Expired
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2013129674A1 (en) * | 2012-03-01 | 2013-09-06 | 学校法人兵庫医科大学 | Novel benzimidazole derivative and use thereof |
| JPWO2013129674A1 (en) * | 2012-03-01 | 2015-07-30 | 学校法人兵庫医科大学 | Novel benzimidazole derivatives and uses thereof |
| US9212169B2 (en) | 2012-03-01 | 2015-12-15 | Hyogo College Of Medicine | Benzimidazole derivative and use thereof |
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