GB703669A - Improvements in or relating to the production of 3-pyrazolidones - Google Patents
Improvements in or relating to the production of 3-pyrazolidonesInfo
- Publication number
- GB703669A GB703669A GB2428551A GB2428551A GB703669A GB 703669 A GB703669 A GB 703669A GB 2428551 A GB2428551 A GB 2428551A GB 2428551 A GB2428551 A GB 2428551A GB 703669 A GB703669 A GB 703669A
- Authority
- GB
- United Kingdom
- Prior art keywords
- phenyl
- pyrazolidone
- phenylhydrazine
- ethyl
- hydrogen
- 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 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 4
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 abstract 3
- 125000001183 hydrocarbyl group Chemical group 0.000 abstract 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 3
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 abstract 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 239000003795 chemical substances by application Substances 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 abstract 2
- CBDMBBKKGFKNCA-UHFFFAOYSA-N 1,5-diphenylpyrazolidin-3-one Chemical compound N1C(=O)CC(C=2C=CC=CC=2)N1C1=CC=CC=C1 CBDMBBKKGFKNCA-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
- TWAVNLQGWZQKHD-UHFFFAOYSA-N 5,5-dimethyl-1-phenylpyrazolidin-3-one Chemical compound CC1(C)CC(=O)NN1C1=CC=CC=C1 TWAVNLQGWZQKHD-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
- 239000004215 Carbon black (E152) Substances 0.000 abstract 1
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 abstract 1
- KBEBGUQPQBELIU-CMDGGOBGSA-N Ethyl cinnamate Chemical compound CCOC(=O)\C=C\C1=CC=CC=C1 KBEBGUQPQBELIU-CMDGGOBGSA-N 0.000 abstract 1
- ZFDIRQKJPRINOQ-HWKANZROSA-N Ethyl crotonate Chemical compound CCOC(=O)\C=C\C ZFDIRQKJPRINOQ-HWKANZROSA-N 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 abstract 1
- 239000003513 alkali Substances 0.000 abstract 1
- 150000004703 alkoxides Chemical class 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 229910002092 carbon dioxide Inorganic materials 0.000 abstract 1
- 239000001569 carbon dioxide Substances 0.000 abstract 1
- KBEBGUQPQBELIU-UHFFFAOYSA-N cinnamic acid ethyl ester Natural products CCOC(=O)C=CC1=CC=CC=C1 KBEBGUQPQBELIU-UHFFFAOYSA-N 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 229930195733 hydrocarbon Natural products 0.000 abstract 1
- 150000002430 hydrocarbons Chemical class 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-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
- ZFDIRQKJPRINOQ-UHFFFAOYSA-N transbutenic acid ethyl ester Natural products CCOC(=O)C=CC ZFDIRQKJPRINOQ-UHFFFAOYSA-N 0.000 abstract 1
Landscapes
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
3-Pyrazolidones of the general formula <FORM:0703669/IV(b)/1> are prepared by reacting a hydrazine RNH-NH2 with an ester <FORM:0703669/IV(b)/2> where R1 and R3 are hydrogen atoms or hydrocarbon groups, R and R2 are hydrogen atoms or hydrocarbon or substituted hydrocarbon groups, and R4 is a hydrocarbon group. In the preferred form, R is a phenyl or substituted phenyl group, R1 and R3 are hydrogen or alkyl groups, R2 is hydrogen or a phenyl or substituted phenyl group and R4 is an alkyl group having up to 4 carbon atoms. The reaction may be carried out in anhydrous conditions in the presence of a basic condensing agent such as an alkali alkoxide or hydroxide, and the product separated by passing carbon dioxide into the mixture. Examples are given of the preparation of (1) 1-phenyl-3-pyrazolidone from ethyl acrylate and phenylhydrazine (a) in the absence of a condensing agent, and in the presence of (b) triethylamine, and (c) sodium ethoxide, the yields increasing in that order, (2) 1-phenyl-4-methyl-3-pyrazolidone from methyl methacrylate and phenylhydrazine (3) 1-phenyl-5-methyl-3-pyrazolidone from ethyl crotonate and phenylhydrazine, (4) 1-phenyl-5, 5-dimethyl-3-pyrazolidone from ethyl b b -dimethylacrylate and phenylhydrazine, and (5) 1, 5-diphenyl-3-pyrazolidone from ethyl cinnamate and phenylhydrazine, Examples (2) to (5) being effected in the presence of sodium ethoxide.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2428551A GB703669A (en) | 1951-10-17 | 1951-10-17 | Improvements in or relating to the production of 3-pyrazolidones |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2428551A GB703669A (en) | 1951-10-17 | 1951-10-17 | Improvements in or relating to the production of 3-pyrazolidones |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB703669A true GB703669A (en) | 1954-02-10 |
Family
ID=10209297
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2428551A Expired GB703669A (en) | 1951-10-17 | 1951-10-17 | Improvements in or relating to the production of 3-pyrazolidones |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB703669A (en) |
-
1951
- 1951-10-17 GB GB2428551A patent/GB703669A/en not_active Expired
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