GB1093281A - 3-pyrazolidones and their use as photographic developers - Google Patents
3-pyrazolidones and their use as photographic developersInfo
- Publication number
- GB1093281A GB1093281A GB1156063A GB1156063A GB1093281A GB 1093281 A GB1093281 A GB 1093281A GB 1156063 A GB1156063 A GB 1156063A GB 1156063 A GB1156063 A GB 1156063A GB 1093281 A GB1093281 A GB 1093281A
- Authority
- GB
- United Kingdom
- Prior art keywords
- group
- hydroxyalkyl
- give
- aryl
- acid
- 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
- NDGRWYRVNANFNB-UHFFFAOYSA-N pyrazolidin-3-one Chemical class O=C1CCNN1 NDGRWYRVNANFNB-UHFFFAOYSA-N 0.000 title 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 abstract 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 3
- 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 abstract 2
- OFLXLNCGODUUOT-UHFFFAOYSA-N acetohydrazide Chemical compound C\C(O)=N\N OFLXLNCGODUUOT-UHFFFAOYSA-N 0.000 abstract 2
- -1 acetyl halide Chemical class 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 229910021529 ammonia Inorganic materials 0.000 abstract 2
- 238000000034 method Methods 0.000 abstract 2
- XBYRMPXUBGMOJC-UHFFFAOYSA-N 1,2-dihydropyrazol-3-one Chemical class OC=1C=CNN=1 XBYRMPXUBGMOJC-UHFFFAOYSA-N 0.000 abstract 1
- IZTBARLEKCMPRU-UHFFFAOYSA-N 4,4-bis(hydroxymethyl)-1-(4-methylphenyl)pyrazolidin-3-one Chemical compound C1=CC(C)=CC=C1N1NC(=O)C(CO)(CO)C1 IZTBARLEKCMPRU-UHFFFAOYSA-N 0.000 abstract 1
- AJKLCDRWGVLVSH-UHFFFAOYSA-N 4,4-bis(hydroxymethyl)-1-phenylpyrazolidin-3-one Chemical compound N1C(=O)C(CO)(CO)CN1C1=CC=CC=C1 AJKLCDRWGVLVSH-UHFFFAOYSA-N 0.000 abstract 1
- DSVIHYOAKPVFEH-UHFFFAOYSA-N 4-(hydroxymethyl)-4-methyl-1-phenylpyrazolidin-3-one Chemical compound N1C(=O)C(C)(CO)CN1C1=CC=CC=C1 DSVIHYOAKPVFEH-UHFFFAOYSA-N 0.000 abstract 1
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 150000001555 benzenes Chemical class 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine Substances NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 abstract 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 abstract 1
- HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 abstract 1
- 229940067157 phenylhydrazine Drugs 0.000 abstract 1
- 238000010992 reflux Methods 0.000 abstract 1
- 238000006798 ring closing metathesis reaction Methods 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- 125000000547 substituted alkyl group Chemical group 0.000 abstract 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 abstract 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C243/00—Compounds containing chains of nitrogen atoms singly-bound to each other, e.g. hydrazines, triazanes
-
- 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
- C07D231/06—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D231/08—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with oxygen or sulfur atoms directly attached to ring carbon atoms
-
- 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
- G03C5/00—Photographic processes or agents therefor; Regeneration of such processing agents
- G03C5/26—Processes using silver-salt-containing photosensitive materials or agents therefor
- G03C5/29—Development processes or agents therefor
- G03C5/30—Developers
- G03C5/3028—Heterocyclic compounds
- G03C5/3035—Heterocyclic compounds containing a diazole ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
The invention comprises 2-pyrazolidones of the general formula <FORM:1093281/C2/1> in which R1 is a hydroxyalkyl group, R2 is an alkyl, hydroxyalkyl or substituted alkyl group in which the alkyl group contains 1-4 carbon atoms, and R3 is an aryl group. The compounds of the above formula in which both R1 and R2 are hydroxyalkyl can be made by first reacting under reflux an acetoxymethyl-dilacetoxyalkyl) acetyl halide with an aryl hydrazine, which may be substituted in the benzene nucleus, to form a 1 - aryl - 2 - [2 - acetoxymethyl - 2,2 - di-(acetoxyalkyl) acet] hydrazide which is treated with ammonia to form the corresponding 1-aryl-2 - [2 - hydroxy methyl - 2,2 - di - (hydroxyalkyl) - acet] - hydrazide which is then subjected to ring closure. Those compounds in which R2 is not an hydroxy alkyl group may be made by an analogous method using as starting material a compound containing one acetoxyalkyl group and the required group R2 instead of the second acetoxyalkyl group. In the examples (a) pentaerythritol is oxidized to trihydroxymethylaceti acid; this is treated with acetic anhydride to give triacetoxyacetic acid and this is reacted with sulphuryl chloride to give the acid chloride; the acid chloride is reacted with phenylhydrazine to give the acethydrazide; the acethydrazide is treated with ammonia to form 1-phenyl-2,2,2-trihydroxymethyl - acethydrazide and this is heated with anhydrous p-toluene sulphonic acid to give 4,4 - dihydroxymethyl - 1 - phenylpyrazolid - 3 - one; and (b) 4,4 - dihydroxymethyl - 1 - p - tolylpyrazolid - 3 - one and 4-hydroxymethyl - 4 - methyl - 1 - phenylpyrazolid-3-one are prepared by analogous methods.
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1156063A GB1093281A (en) | 1963-03-22 | 1963-03-22 | 3-pyrazolidones and their use as photographic developers |
| NL6602986A NL6602986A (en) | 1963-03-22 | 1966-03-08 |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1156063A GB1093281A (en) | 1963-03-22 | 1963-03-22 | 3-pyrazolidones and their use as photographic developers |
| NL6602986A NL6602986A (en) | 1963-03-22 | 1966-03-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1093281A true GB1093281A (en) | 1967-11-29 |
Family
ID=26248360
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1156063A Expired GB1093281A (en) | 1963-03-22 | 1963-03-22 | 3-pyrazolidones and their use as photographic developers |
Country Status (2)
| Country | Link |
|---|---|
| GB (1) | GB1093281A (en) |
| NL (1) | NL6602986A (en) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4209580A (en) * | 1978-10-02 | 1980-06-24 | Eastman Kodak Company | Substituted 1-phenyl-3-pyrazolidinone electron transfer agents |
| US4266002A (en) * | 1978-10-02 | 1981-05-05 | Eastman Kodak Company | Substituted 1-phenyl-3-pyrazolidinone electron transfer agents |
| DE3104176A1 (en) * | 1980-02-08 | 1981-12-10 | Fuji Photo Film Co., Ltd., Minami-Ashigara, Kanagawa | METHOD FOR PRODUCING PRINTING PLATES |
| EP0054002A1 (en) * | 1980-12-10 | 1982-06-16 | Ciba-Geigy Ag | Process for the preparation of 3-pyrazolidinones, and their use in photographic developing baths |
| US4345019A (en) | 1980-04-23 | 1982-08-17 | Mitsubishi Paper Mills, Ltd. | Diffusion transfer process |
| EP0134695A1 (en) * | 1983-08-04 | 1985-03-20 | EASTMAN KODAK COMPANY (a New Jersey corporation) | Photographic element containing a 4-hydroxyalkyl-substituted 1-phenyl-3-pyrazolidinone electron transfer agent |
| US5187050A (en) * | 1986-11-07 | 1993-02-16 | Fuji Photo Film Co., Ltd. | Method for automatic processing of silver halide photographic material |
-
1963
- 1963-03-22 GB GB1156063A patent/GB1093281A/en not_active Expired
-
1966
- 1966-03-08 NL NL6602986A patent/NL6602986A/xx unknown
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4209580A (en) * | 1978-10-02 | 1980-06-24 | Eastman Kodak Company | Substituted 1-phenyl-3-pyrazolidinone electron transfer agents |
| EP0009837A3 (en) * | 1978-10-02 | 1981-04-15 | Eastman Kodak Company | Photographic element containing substituted 1-phenyl-3-pyrazolidinone electron transfer agent |
| US4266002A (en) * | 1978-10-02 | 1981-05-05 | Eastman Kodak Company | Substituted 1-phenyl-3-pyrazolidinone electron transfer agents |
| DE3104176A1 (en) * | 1980-02-08 | 1981-12-10 | Fuji Photo Film Co., Ltd., Minami-Ashigara, Kanagawa | METHOD FOR PRODUCING PRINTING PLATES |
| US4345019A (en) | 1980-04-23 | 1982-08-17 | Mitsubishi Paper Mills, Ltd. | Diffusion transfer process |
| EP0054002A1 (en) * | 1980-12-10 | 1982-06-16 | Ciba-Geigy Ag | Process for the preparation of 3-pyrazolidinones, and their use in photographic developing baths |
| EP0134695A1 (en) * | 1983-08-04 | 1985-03-20 | EASTMAN KODAK COMPANY (a New Jersey corporation) | Photographic element containing a 4-hydroxyalkyl-substituted 1-phenyl-3-pyrazolidinone electron transfer agent |
| US5187050A (en) * | 1986-11-07 | 1993-02-16 | Fuji Photo Film Co., Ltd. | Method for automatic processing of silver halide photographic material |
Also Published As
| Publication number | Publication date |
|---|---|
| NL6602986A (en) | 1967-09-11 |
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