GB1236767A - Benzoylacetamide derivatives and their use in colour photography - Google Patents
Benzoylacetamide derivatives and their use in colour photographyInfo
- Publication number
- GB1236767A GB1236767A GB34341/68A GB3434168A GB1236767A GB 1236767 A GB1236767 A GB 1236767A GB 34341/68 A GB34341/68 A GB 34341/68A GB 3434168 A GB3434168 A GB 3434168A GB 1236767 A GB1236767 A GB 1236767A
- Authority
- GB
- United Kingdom
- Prior art keywords
- trifluoro
- chloroethoxy
- acetanilide
- acid
- benzoyl
- 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
- RTLKJCSGNBYCKJ-UHFFFAOYSA-N 3-oxo-3-phenylpropanamide Chemical class NC(=O)CC(=O)C1=CC=CC=C1 RTLKJCSGNBYCKJ-UHFFFAOYSA-N 0.000 title abstract 3
- -1 -CHFCl Chemical class 0.000 abstract 12
- 229960001413 acetanilide Drugs 0.000 abstract 7
- FZERHIULMFGESH-UHFFFAOYSA-N methylenecarboxanilide Natural products CC(=O)NC1=CC=CC=C1 FZERHIULMFGESH-UHFFFAOYSA-N 0.000 abstract 6
- 229910052739 hydrogen Inorganic materials 0.000 abstract 4
- 239000001257 hydrogen Substances 0.000 abstract 4
- 125000001424 substituent group Chemical group 0.000 abstract 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 3
- 239000002253 acid Substances 0.000 abstract 3
- WPRFIGFRAYZJQB-UHFFFAOYSA-N 3-amino-4-hexadecoxybenzoic acid Chemical compound NC=1C=C(C(=O)O)C=CC1OCCCCCCCCCCCCCCCC WPRFIGFRAYZJQB-UHFFFAOYSA-N 0.000 abstract 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 2
- 239000005864 Sulphur Substances 0.000 abstract 2
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical group O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 125000003118 aryl group Chemical group 0.000 abstract 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 230000007062 hydrolysis Effects 0.000 abstract 2
- 238000006460 hydrolysis reaction Methods 0.000 abstract 2
- 239000000543 intermediate Substances 0.000 abstract 2
- VUWZXQFDWMHYSG-UHFFFAOYSA-N methyl 2-(2-chloro-1,1,2-trifluoroethoxy)-4-methoxybenzoate Chemical compound COC(C1=C(C=C(C=C1)OC)OC(C(Cl)F)(F)F)=O VUWZXQFDWMHYSG-UHFFFAOYSA-N 0.000 abstract 2
- ZICRWXFGZCVTBZ-UHFFFAOYSA-N methyl 4-methoxy-salicylate Natural products COC(=O)C1=CC=C(OC)C=C1O ZICRWXFGZCVTBZ-UHFFFAOYSA-N 0.000 abstract 2
- 229910052760 oxygen Inorganic materials 0.000 abstract 2
- 239000001301 oxygen Substances 0.000 abstract 2
- DJDQNISEJVPQCS-UHFFFAOYSA-N 1-(difluoromethoxy)-4-methylbenzene Chemical compound CC1=CC=C(OC(F)F)C=C1 DJDQNISEJVPQCS-UHFFFAOYSA-N 0.000 abstract 1
- HNTGIJLWHDPAFN-UHFFFAOYSA-N 1-bromohexadecane Chemical compound CCCCCCCCCCCCCCCCBr HNTGIJLWHDPAFN-UHFFFAOYSA-N 0.000 abstract 1
- ASIHNHGLHLZCOJ-UHFFFAOYSA-N 2-(2-chloro-1,1,2-trifluoroethoxy)benzoyl chloride Chemical compound FC(C(Cl)F)(OC1=C(C(=O)Cl)C=CC=C1)F ASIHNHGLHLZCOJ-UHFFFAOYSA-N 0.000 abstract 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical class CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 abstract 1
- DUXJZEFQBCJLBY-UHFFFAOYSA-N 3-[2-(2-chloro-1,1,2-trifluoroethyl)sulfanylphenyl]-N-[4-(4-methoxyphenyl)-5-tetradecyl-1,3-thiazol-2-yl]-3-oxopropanamide Chemical compound FC(C(Cl)F)(SC1=C(C(=O)CC(=O)NC=2SC(=C(N2)C2=CC=C(C=C2)OC)CCCCCCCCCCCCCC)C=CC=C1)F DUXJZEFQBCJLBY-UHFFFAOYSA-N 0.000 abstract 1
- BSNNYLYELGBSBA-UHFFFAOYSA-N 4-(difluoromethoxy)benzoic acid Chemical compound OC(=O)C1=CC=C(OC(F)F)C=C1 BSNNYLYELGBSBA-UHFFFAOYSA-N 0.000 abstract 1
- BRXHGTQXWFFHMM-UHFFFAOYSA-N 4-(difluoromethoxy)benzoyl chloride Chemical compound FC(F)OC1=CC=C(C(Cl)=O)C=C1 BRXHGTQXWFFHMM-UHFFFAOYSA-N 0.000 abstract 1
- RWNIUYMYGCATIY-UHFFFAOYSA-N FC(C(Cl)F)(OC1=C(C(=O)Cl)C=CC(=C1)OC)F.S(=O)(Cl)Cl Chemical compound FC(C(Cl)F)(OC1=C(C(=O)Cl)C=CC(=C1)OC)F.S(=O)(Cl)Cl RWNIUYMYGCATIY-UHFFFAOYSA-N 0.000 abstract 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 abstract 1
- 125000004663 dialkyl amino group Chemical group 0.000 abstract 1
- OKVAEDRIJKEGMK-UHFFFAOYSA-N ethyl 3-[2-(2-chloro-1,1,2-trifluoroethoxy)-4-methoxyphenyl]-3-oxopropanoate Chemical compound C(C)OC(CC(C1=C(C=C(C=C1)OC)OC(C(Cl)F)(F)F)=O)=O OKVAEDRIJKEGMK-UHFFFAOYSA-N 0.000 abstract 1
- MZCUMXTULLRQSK-UHFFFAOYSA-N ethyl 3-[2-(2-chloro-1,1,2-trifluoroethoxy)phenyl]-3-oxopropanoate Chemical compound C(C)OC(CC(C1=C(C=CC=C1)OC(C(Cl)F)(F)F)=O)=O MZCUMXTULLRQSK-UHFFFAOYSA-N 0.000 abstract 1
- HSLDDVSXVCYKBZ-UHFFFAOYSA-N ethyl 3-[4-(2-chloro-1,1,2-trifluoroethoxy)phenyl]-3-oxopropanoate Chemical compound C(C)OC(CC(C1=CC=C(C=C1)OC(C(Cl)F)(F)F)=O)=O HSLDDVSXVCYKBZ-UHFFFAOYSA-N 0.000 abstract 1
- DSXLEFYJLVDGQX-UHFFFAOYSA-N ethyl 3-[4-(difluoromethoxy)phenyl]-3-oxopropanoate Chemical compound C(C)OC(CC(C1=CC=C(C=C1)OC(F)F)=O)=O DSXLEFYJLVDGQX-UHFFFAOYSA-N 0.000 abstract 1
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 abstract 1
- 229910052731 fluorine Inorganic materials 0.000 abstract 1
- 239000011737 fluorine Substances 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 150000002431 hydrogen Chemical class 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- ZQCZJCFITKBNOA-UHFFFAOYSA-N methyl 2-(2-chloro-1,1,2-trifluoroethyl)sulfanylbenzoate Chemical compound COC(C1=C(C=CC=C1)SC(C(Cl)F)(F)F)=O ZQCZJCFITKBNOA-UHFFFAOYSA-N 0.000 abstract 1
- WRGLZAJBHUOPFO-UHFFFAOYSA-N methyl 3-oxo-3-phenylpropanoate Chemical compound COC(=O)CC(=O)C1=CC=CC=C1 WRGLZAJBHUOPFO-UHFFFAOYSA-N 0.000 abstract 1
- GNCWCTBHZCBXGL-UHFFFAOYSA-N methyl 4-hydroxy-3-nitrobenzoate Chemical compound COC(=O)C1=CC=C(O)C([N+]([O-])=O)=C1 GNCWCTBHZCBXGL-UHFFFAOYSA-N 0.000 abstract 1
- 150000002828 nitro derivatives Chemical class 0.000 abstract 1
- 230000001590 oxidative effect Effects 0.000 abstract 1
- 125000006684 polyhaloalkyl group Polymers 0.000 abstract 1
- 239000012286 potassium permanganate Substances 0.000 abstract 1
- XMVJITFPVVRMHC-UHFFFAOYSA-N roxarsone Chemical compound OC1=CC=C([As](O)(O)=O)C=C1[N+]([O-])=O XMVJITFPVVRMHC-UHFFFAOYSA-N 0.000 abstract 1
- 159000000000 sodium salts Chemical class 0.000 abstract 1
- 239000000126 substance Substances 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
- G03C7/362—Benzoyl-acetanilide couplers
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Silver Salt Photography Or Processing Solution Therefor (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
1,236,767. Fluorinated benzoylacetamide derivatives. GEVAERT-AGFA N.V. 20 June, 1969 [18 July, 1968], No. 34341/68. Heading C2C. [Also in Division G2] The invention comprises benzoylacetamide derivatives containing at least one substituent of the formula RCF 2 Q-, in which Q denotes oxygen, sulphur or sulphonyl and R denotes hydrogen, fluorine or polyhaloalkyl, e.g. -CHFCl, -CFCl 2 or -CHFCF 3 . More particularly, the invention comprises compounds of the formula in which R and Q are as defined above, X denotes hydrogen or a substituent, examples of which are given, Z 1 denotes hydrogen or halogen, a group RCF 2 Q- or an alkyl, alkoxy or a dialkylamino group and A denotes an aromatic or heterocyclic nucleus, preferably carrying a substituent -YD, in which D denotes an acyclic hydrocarbon residue of 5-20 carbon atoms and Y denotes a chemical bond, oxygen, sulphur, sulphonyl, -N- (alkyl)-,-CONH-,-NHCO-,-N(R 3 )SO 2 - or -SO 2 N(R 3 )-, R 3 denoting hydrogen or alkyl. The nucleus A may also carry additional substituents, a number of which are specified. The compounds are obtainable by condensing an appropriately substituted benzoylacetic acid ester with appropriate aromatic or heterocyclic amines. Thus, o-(1,1,2-trifluoro-2-chlorethoxy) - benzoyl - (2<SP>1</SP> - hexadecyloxy - 5<SP>1</SP>- carboxy)-acetanilide is obtained from o-(1,1,2- trifluoro - 2 - chloroethoxy) - benzoylacetic acid ethyl ester and 3-amino-4-hexadecyloxybenzoic acid. Other specified products of the invention are p - difluoromethoxybenzoyl - (2<SP>1 </SP>- hexadecyloxy - 5 - carboxy) - acetanilide, o - (1,1,2- trifluoro - 2 - chloroethoxy) - p - methoxybenzoyl - (2<SP>1</SP> - hexadecyloxy - 5<SP>1</SP> - fluorosulphonyl) - acetanilide, o - (1,1,2 - trifluoro- 2 - chloroethoxy) - p - methoxy - benzoyl - (21- hexadecyloxy - 5 - sulpho) - acetanilide potassium salt, o,p - di - (1,1,2 - trifluoro - 2 - chloroethoxy) - benzoyl - (21 - hexadecyloxy - 51 - fluorosulphonyl) - acetanilide, o,p - di - (1,1,2- trifluoro - 2 - chloroethoxy) - benzoyl - (2<SP>1</SP> - hexadecyloxy - 5<SP>1 </SP>- sulpho) - acetanilide potassium salt, p - (1,1,2 - trifluoro - 2 - chloroethoxy) - benzoyl - (2<SP>1</SP>- dodecyloxy) - acetanilide, o - (1,1,2 - trifluoro - 2 - chloroethoxythio) - benzoyl - (2<SP>1 </SP>- hexadecyloxy - 5<SP>1 </SP>- carboxy) - acetanilide, o - (1,1,2 - trifluoro - 2 - chloroethoxy) - p - methoxybenzoyl - [2<SP>1</SP> - chloro - 5<SP>1</SP> - (N - methyl - N - hexadecylsulphamoyl)] - acetanilide and 2 - [o - (1,1,2- trifluoro - 2 - chloroethylthio) - benzoylacetamido] - 4 - p - methoxyphenyl - 5 - tetradecylthiazole. The products are useful in colour photography (see Division G2). The preparation of the following intermediates is described. o- or p-(1,1,2-Trifluoro-2-chloroethoxy)-benzoylacetic acid ethyl ester is prepared from o- (1,1,2 - trifluoro - 2 - chloroethoxy) - benzoyl chloride and the sodium salt of ethyl acetoacetate. Other intermediates are obtained analogously from p-difluoromethoxybenzoylacetic acid ethyl ester, o-(1,1,2-trifluoro-2- chloroethoxy) - p - methoxybenzoyl acetic acid ethyl ester and o,p-di-(1,1,2-trifluoro-2-chloroethoxy)-benzoylacetic acid ethyl ester. o - (1,1,2 - Trifluoro - 2 - chloroethoxy) - p - methoxybenzoic acid methyl ester is obtainable from 2 - hydroxy - 4 - methoxybenzoic acid methyl ester by the method of Lichtenberger. It yields the free acid on hydrolysis. o,p-Di- (1,1,2 - trifluoro - 2 - chloroethoxy) - benzoic acid methyl ester is prepared similarly, and can be similarly hydrolysed. o - (1,1,2 - Trifluoro - 2 - chloroethoxythio). benzoylacetic acid methyl ester is obtainable from o - (1,1,2 - trifluoro - 2 - chloroethylthio)- benzoic acid methyl ester analogously to o- (1,1,2 - trifluoro - 2 - chloroethoxy) - p - methoxybenzoic acid methyl ester above. 3 - Nitro - 4 - hexadecylorybenzoic acid is obtainable from 3-nitro-4-hydroxybenzoic acid methyl ester and hexadecyl bromide, followed by hydrolysis. 3 - Amino - 4 - hexadecyloxybenzoic acid is obtained by catalytic hydrogenation of the corresponding nitro compound. p-Difluoromethoxybenzoic acid is prepared by oxidizing p-tolyl difluoromethyl ether with potassium permanganate. p-Difluoromethoxybenzoyl chloride is prepared from the corresponding acid and thionyl chloride o - (1,1,2 - Trifluoro - 2 - chloroethoxy)- p - methoxybenzoyl chloride and o,p - di - (1,1,2- trifluoro - 2 - chloroethoxy) - benzoyl chloride are prepared similarly.
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB34341/68A GB1236767A (en) | 1968-07-18 | 1968-07-18 | Benzoylacetamide derivatives and their use in colour photography |
| US837299A US3660095A (en) | 1968-07-18 | 1969-06-27 | Photographic silver halide color material utilizing benzoylacetamide color couplers |
| FR6923966A FR2013174A1 (en) | 1968-07-18 | 1969-07-11 | |
| DE19691935911 DE1935911A1 (en) | 1968-07-18 | 1969-07-15 | Color photographic material |
| BE736253D BE736253A (en) | 1968-07-18 | 1969-07-18 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB34341/68A GB1236767A (en) | 1968-07-18 | 1968-07-18 | Benzoylacetamide derivatives and their use in colour photography |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1236767A true GB1236767A (en) | 1971-06-23 |
Family
ID=10364441
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB34341/68A Expired GB1236767A (en) | 1968-07-18 | 1968-07-18 | Benzoylacetamide derivatives and their use in colour photography |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US3660095A (en) |
| BE (1) | BE736253A (en) |
| DE (1) | DE1935911A1 (en) |
| FR (1) | FR2013174A1 (en) |
| GB (1) | GB1236767A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5412220B2 (en) * | 1974-04-12 | 1979-05-21 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2895826A (en) * | 1956-10-08 | 1959-07-21 | Eastman Kodak Co | Photographic color couplers containing fluoroalkylcarbonamido groups |
| GB894068A (en) * | 1959-09-17 | 1962-04-18 | Gen Aniline & Film Corp | Improvements in or relating to color photography |
| BE634669A (en) * | 1963-07-09 | 1964-01-09 |
-
1968
- 1968-07-18 GB GB34341/68A patent/GB1236767A/en not_active Expired
-
1969
- 1969-06-27 US US837299A patent/US3660095A/en not_active Expired - Lifetime
- 1969-07-11 FR FR6923966A patent/FR2013174A1/fr not_active Withdrawn
- 1969-07-15 DE DE19691935911 patent/DE1935911A1/en active Pending
- 1969-07-18 BE BE736253D patent/BE736253A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| FR2013174A1 (en) | 1970-03-27 |
| DE1935911A1 (en) | 1970-01-22 |
| US3660095A (en) | 1972-05-02 |
| BE736253A (en) | 1970-01-19 |
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