GB728368A - Improvements in or relating to the production of 3-pyrazolidones - Google Patents
Improvements in or relating to the production of 3-pyrazolidonesInfo
- Publication number
- GB728368A GB728368A GB2128152A GB2128152A GB728368A GB 728368 A GB728368 A GB 728368A GB 2128152 A GB2128152 A GB 2128152A GB 2128152 A GB2128152 A GB 2128152A GB 728368 A GB728368 A GB 728368A
- Authority
- GB
- United Kingdom
- Prior art keywords
- pyrazolidone
- phenyl
- reacted
- give
- phenylhydrazine
- 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 abstract 2
- HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 abstract 6
- 229940067157 phenylhydrazine Drugs 0.000 abstract 6
- 125000000217 alkyl group Chemical group 0.000 abstract 4
- 125000003118 aryl group Chemical group 0.000 abstract 3
- 229910052739 hydrogen Inorganic materials 0.000 abstract 3
- 239000001257 hydrogen Substances 0.000 abstract 3
- ACEIBVGIYJKQBL-UHFFFAOYSA-N 5,5-diphenylpyrazolidin-3-one Chemical compound N1NC(=O)CC1(C=1C=CC=CC=1)C1=CC=CC=C1 ACEIBVGIYJKQBL-UHFFFAOYSA-N 0.000 abstract 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- PASQTEDKDMHJPQ-UHFFFAOYSA-N 1-(4-chlorophenyl)-4-methylpyrazolidin-3-one Chemical compound N1C(=O)C(C)CN1C1=CC=C(Cl)C=C1 PASQTEDKDMHJPQ-UHFFFAOYSA-N 0.000 abstract 1
- QEWLOWAUHUOAEK-UHFFFAOYSA-N 1-(4-chlorophenyl)pyrazolidin-3-one Chemical compound C1=CC(Cl)=CC=C1N1NC(=O)CC1 QEWLOWAUHUOAEK-UHFFFAOYSA-N 0.000 abstract 1
- SVJPLZNMCJQWPJ-UHFFFAOYSA-N 1-(4-methylphenyl)pyrazolidin-3-one Chemical compound C1=CC(C)=CC=C1N1NC(=O)CC1 SVJPLZNMCJQWPJ-UHFFFAOYSA-N 0.000 abstract 1
- IENJOZLUZVMJDE-UHFFFAOYSA-N 1-[(4-methoxyphenyl)methyl]pyrazolidin-3-one Chemical compound C1=CC(OC)=CC=C1CN1NC(=O)CC1 IENJOZLUZVMJDE-UHFFFAOYSA-N 0.000 abstract 1
- ZZEYCGJAYIHIAZ-UHFFFAOYSA-N 4-methyl-1-phenylpyrazolidin-3-one Chemical compound N1C(=O)C(C)CN1C1=CC=CC=C1 ZZEYCGJAYIHIAZ-UHFFFAOYSA-N 0.000 abstract 1
- FIARATPVIIDWJT-UHFFFAOYSA-N 5-methyl-1-phenylpyrazolidin-3-one Chemical compound CC1CC(=O)NN1C1=CC=CC=C1 FIARATPVIIDWJT-UHFFFAOYSA-N 0.000 abstract 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- -1 alkali metal alkoxide Chemical class 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 150000001408 amides Chemical class 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- 239000002585 base Substances 0.000 abstract 1
- 229910052736 halogen Chemical group 0.000 abstract 1
- 150000002367 halogens Chemical group 0.000 abstract 1
- 150000002431 hydrogen Chemical class 0.000 abstract 1
- SWPMNMYLORDLJE-UHFFFAOYSA-N n-ethylprop-2-enamide Chemical compound CCNC(=O)C=C SWPMNMYLORDLJE-UHFFFAOYSA-N 0.000 abstract 1
- CMCWWLVWPDLCRM-UHFFFAOYSA-N phenidone Chemical compound N1C(=O)CCN1C1=CC=CC=C1 CMCWWLVWPDLCRM-UHFFFAOYSA-N 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- APEJMQOBVMLION-VOTSOKGWSA-N trans-cinnamamide Chemical compound NC(=O)\C=C\C1=CC=CC=C1 APEJMQOBVMLION-VOTSOKGWSA-N 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
- 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
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
3-Pyrazolidones of the general formula <FORM:0728368/IV (b)/1> are made by reacting a hydrazine of the general formula RNH.NH2 with an amide of the general formula <FORM:0728368/IV (b)/2> where R is an aryl group or an aryl group substituted by alkyl, alkoxy or halogen, R1 is hydrogen or alkyl, R2 and R4 are hydrogen, alkyl, aryl or aralkyl, and R3 is hydrogen or alkyl. The reaction is preferably carried out in the presence of at least an equimolecular proportion of a strong base such as an alkali metal alkoxide. R is preferably a phenyl group. In examples (1) a -methylacrylamide is reacted with phenyl hydrazine to give 4-methyl-1-phenyl-3-pyrazolidone; (2) acrylamide is reacted with phenyl hydrazine to give 1-phenyl-3-pyrazolidone; (3) N-ethylacrylamide is reacted with phenylhydrazine to give the product of (2); (4) cinnamide is reacted with phenylhydrazine to give 1 : 5-diphenyl-3-pyrazolidone; (5) b : b -dimethylacrylethylamide is reacted with phenylhydrazine to give 5 : 5-dimethyl-1-phenyl-3-pyrazolidone; (6) crotonamide is reacted with phenylhydrazine to give 5-methyl-1-phenyl-3-pyrazolidone; and (7)-(10) by the same methods there are prepared 1-p-tolyl-3-pyrazolidone; 1 - p - chlorophenyl - 3 - pyrazolidone; 1 - p - anisyl - 3 - pyrazolidone and 1 - p-chlorophenyl - 4 - methyl - 3 - pyrazolidone.
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2128152A GB728368A (en) | 1952-08-25 | 1952-08-25 | Improvements in or relating to the production of 3-pyrazolidones |
| DEI7614A DE1048921B (en) | 1952-08-25 | 1953-08-19 | Process for the preparation of 1-phenyl-3-pyrazolidone |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2128152A GB728368A (en) | 1952-08-25 | 1952-08-25 | Improvements in or relating to the production of 3-pyrazolidones |
| GB2534152 | 1952-10-09 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB728368A true GB728368A (en) | 1955-04-20 |
Family
ID=26255243
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2128152A Expired GB728368A (en) | 1952-08-25 | 1952-08-25 | Improvements in or relating to the production of 3-pyrazolidones |
Country Status (2)
| Country | Link |
|---|---|
| DE (1) | DE1048921B (en) |
| GB (1) | GB728368A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106866531A (en) * | 2017-04-17 | 2017-06-20 | 安徽广信农化股份有限公司 | A kind of synthesis technique of pyraclostrobin intermediate pyrazole alkanone |
| CN106977456A (en) * | 2017-04-17 | 2017-07-25 | 安徽广信农化股份有限公司 | A kind of synthesis system of pyraclostrobin intermediate pyrazole alkanone |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE41936C (en) * | FARBWERKE VORM. Meister, Lucius & Brüning in Höchst a. M | Process for the preparation of oxypyrazole. (I. |
-
1952
- 1952-08-25 GB GB2128152A patent/GB728368A/en not_active Expired
-
1953
- 1953-08-19 DE DEI7614A patent/DE1048921B/en active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106866531A (en) * | 2017-04-17 | 2017-06-20 | 安徽广信农化股份有限公司 | A kind of synthesis technique of pyraclostrobin intermediate pyrazole alkanone |
| CN106977456A (en) * | 2017-04-17 | 2017-07-25 | 安徽广信农化股份有限公司 | A kind of synthesis system of pyraclostrobin intermediate pyrazole alkanone |
Also Published As
| Publication number | Publication date |
|---|---|
| DE1048921B (en) | 1959-01-22 |
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