GB768813A - Substituted 1.2-diphenyl-3.5-dioxo-pyrazolidines and processes for the production thereof - Google Patents
Substituted 1.2-diphenyl-3.5-dioxo-pyrazolidines and processes for the production thereofInfo
- Publication number
- GB768813A GB768813A GB12243/55A GB1224355A GB768813A GB 768813 A GB768813 A GB 768813A GB 12243/55 A GB12243/55 A GB 12243/55A GB 1224355 A GB1224355 A GB 1224355A GB 768813 A GB768813 A GB 768813A
- Authority
- GB
- United Kingdom
- Prior art keywords
- endomethylene
- cyclohexenyl
- methyl
- phenyl
- malonic 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
- 238000000034 method Methods 0.000 title abstract 2
- -1 mono-substituted malonic acid Chemical class 0.000 abstract 13
- 239000002253 acid Substances 0.000 abstract 6
- 150000001875 compounds Chemical class 0.000 abstract 6
- 238000009833 condensation Methods 0.000 abstract 5
- 230000005494 condensation Effects 0.000 abstract 5
- 150000007530 organic bases Chemical class 0.000 abstract 4
- 238000002360 preparation method Methods 0.000 abstract 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 abstract 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 abstract 3
- 150000008064 anhydrides Chemical class 0.000 abstract 3
- 239000004305 biphenyl Substances 0.000 abstract 3
- 235000010290 biphenyl Nutrition 0.000 abstract 3
- 150000007529 inorganic bases Chemical class 0.000 abstract 3
- 239000003960 organic solvent Substances 0.000 abstract 3
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 abstract 3
- 150000003839 salts Chemical class 0.000 abstract 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 abstract 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 abstract 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 abstract 2
- 150000007513 acids Chemical class 0.000 abstract 2
- 239000011230 binding agent Substances 0.000 abstract 2
- 239000003795 chemical substances by application Substances 0.000 abstract 2
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 abstract 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 2
- 239000007858 starting material Substances 0.000 abstract 2
- FWIROFMBWVMWLB-UHFFFAOYSA-N 1-bromo-3-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC(Br)=C1 FWIROFMBWVMWLB-UHFFFAOYSA-N 0.000 abstract 1
- OHXAOPZTJOUYKM-UHFFFAOYSA-N 3-Chloro-2-methylpropene Chemical compound CC(=C)CCl OHXAOPZTJOUYKM-UHFFFAOYSA-N 0.000 abstract 1
- UCJOBPVWCIRPSU-UHFFFAOYSA-N 4-(bromomethyl)cyclohexene Chemical compound BrCC1CCC=CC1 UCJOBPVWCIRPSU-UHFFFAOYSA-N 0.000 abstract 1
- CZGCEKJOLUNIFY-UHFFFAOYSA-N 4-Chloronitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(Cl)C=C1 CZGCEKJOLUNIFY-UHFFFAOYSA-N 0.000 abstract 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 abstract 1
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 abstract 1
- ZPTVNYMJQHSSEA-UHFFFAOYSA-N 4-nitrotoluene Chemical compound CC1=CC=C([N+]([O-])=O)C=C1 ZPTVNYMJQHSSEA-UHFFFAOYSA-N 0.000 abstract 1
- OSDWBNJEKMUWAV-UHFFFAOYSA-N Allyl chloride Chemical compound ClCC=C OSDWBNJEKMUWAV-UHFFFAOYSA-N 0.000 abstract 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 abstract 1
- 239000004215 Carbon black (E152) Substances 0.000 abstract 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 abstract 1
- IYXGSMUGOJNHAZ-UHFFFAOYSA-N Ethyl malonate Chemical class CCOC(=O)CC(=O)OCC IYXGSMUGOJNHAZ-UHFFFAOYSA-N 0.000 abstract 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 abstract 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 229910020667 PBr3 Inorganic materials 0.000 abstract 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 abstract 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 abstract 1
- 229960000583 acetic acid Drugs 0.000 abstract 1
- TUCNEACPLKLKNU-UHFFFAOYSA-N acetyl Chemical group C[C]=O TUCNEACPLKLKNU-UHFFFAOYSA-N 0.000 abstract 1
- 239000003513 alkali Substances 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 150000001340 alkali metals Chemical class 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 125000004414 alkyl thio group Chemical group 0.000 abstract 1
- 150000001408 amides Chemical class 0.000 abstract 1
- 239000007864 aqueous solution Substances 0.000 abstract 1
- INLLPKCGLOXCIV-UHFFFAOYSA-N bromoethene Chemical compound BrC=C INLLPKCGLOXCIV-UHFFFAOYSA-N 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 150000005690 diesters Chemical class 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 239000012362 glacial acetic acid Substances 0.000 abstract 1
- 150000004820 halides Chemical class 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
- 150000004678 hydrides Chemical class 0.000 abstract 1
- 229930195733 hydrocarbon Natural products 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 abstract 1
- 150000004679 hydroxides Chemical class 0.000 abstract 1
- 229940102396 methyl bromide Drugs 0.000 abstract 1
- GZUXJHMPEANEGY-UHFFFAOYSA-N methyl bromide Substances BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- IPNPIHIZVLFAFP-UHFFFAOYSA-N phosphorus tribromide Chemical compound BrP(Br)Br IPNPIHIZVLFAFP-UHFFFAOYSA-N 0.000 abstract 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 abstract 1
- CYMJPJKHCSDSRG-UHFFFAOYSA-N pyrazolidine-3,4-dione Chemical class O=C1CNNC1=O CYMJPJKHCSDSRG-UHFFFAOYSA-N 0.000 abstract 1
- 238000007127 saponification reaction Methods 0.000 abstract 1
- 229910052708 sodium Inorganic materials 0.000 abstract 1
- 239000011734 sodium Substances 0.000 abstract 1
- 159000000000 sodium salts Chemical class 0.000 abstract 1
- 229960004418 trolamine Drugs 0.000 abstract 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention comprises compounds of the general formula <FORM:0768813/IV(b)/1> wherein Ar1 and Ar2 are phenyl radicals which may be substituted by alkyl, alkoxy or alkyl mercapto groups of 1 to 4 carbon atoms or by halogen, R1 and R2 are hydrogen or methyl and n is 0-3, their salts with inorganic or organic bases, and their preparation by (a) condensing, preferably in the presence of an alkaline condensation agent, a diester of the appropriately mono-substituted malonic acid with the appropriate 1,2-diarylhydrazine or an N-acyl derivative thereof or (b) condensing in the presence of an acid binding agent, a dichloride, dibromide or mixed anhydride of the appropriately monosubstituted malonic acid with the appropriate 1 : 2-diarylhydrazine or (c) condensing an appropriately mono-substituted malonic acid mono-ester mono-chloride, bromide or mixed anhydride first, corresponding to (b), with the appropriate diarylhydrazine to form a substituted malonic acid hydrazide ester and then condensing, corresponding to (a), to form the required product, and, if desired, converting the products so obtained into their salts with inorganic or organic bases. Alkaline condensation agents referred to are alkali metals, their alcoholates, amides, hydroxides and hydrides, the condensation preferably being performed in an organic solvent at a raised temperature. Acid binding agents referred to are tertiary organic bases, the condensation being effected with or without organic solvents at temperatures near 0 DEG C., with subsequent heating if desired. Salts according to the invention are prepared by reacting the free pyrazolidinediones in aqueous solution or an organic solvent with an inorganic or organic base, e.g. sodium or potassium hydroxide or carbonate, sodium alcoholate or mono-, di- or tri-ethanolamine or ethylene diamine. Examples describe the preparation of the following 3.5-dioxo-pyrazolidines: 1 : 2 - diphenyl - 4 - (21 : 51 - endomethylene - D 31 - cyclohexenyl - methyl)-, 1 : 2 - di - phenyl - 4 - (21 : 51 - endomethylene - D 31-cyclo-hexenyl)-, 1 : 2 - diphenyl - 4 - (61 - methyl - 21 : 51-endomethylene - D 31 - cyclohexenyl - methyl)-, 1 : 2 - diphenyl - 4 [31 - (211 : 511 - endomethyleneD 311-cyclohexenyl) - propyl - (11)]-, 1 : 2 - di - (p - methyl - phenyl) - 4 - (21 : 51 - endomethylene - D 31 - cyclohexenyl)-, 1 : 2 - di - (p - chlor - phenyl) - 4 - 21 : 51 - endomethylene - D 31 - cyclohexenyl)-, 1 : 2-di-(m-brom-phenyl)-4-(21 : 51-endomethylene - D 31 - cyclohexenyl)-, 1 : 2 - di - (m-methylmercapto) - 4 - [21 : 51 - endomethylene - D 31-cyclohexenyl - (11)]- and 1 : 2 - di - (p - methoxy-phenyl) - 4 - [21 : 51 - endomethylene-D 31-cyclohexenyl - (11)]-; a - (2 : 5 - endomethylene - D 3-cyclohexenyl) - a - carbethoxyacetylhydrazo - benzene is an intermediate in one preparation of the second of the above compounds. The preparation of sodium salts of some of the above compounds is also described. A list of further starting materials is also given, including 4-ethoxy-41-bromo-hydrazobenzene. Starting materials. Compounds of the general formula <FORM:0768813/IV(b)/2> where X is a hydrocarbon radical, are prepared by condensation of sodium malonic acid diesters with the appropriate 21 : 51-endomethylene-D 31-cyclohexenyl-alkyl halides, themselves prepared by the addition of cyclopentadiene to unsaturated aliphatic halogen compounds such as vinyl bromide, allyl chloride or methallyl chloride. Acid halides are obtained from the above esters by alkaline saponification, liberation of the acids and treatment thereof with inorganic acid halides. Mixed anhydrides, when X is an acetyl radical, are obtained from the free acid and excess acetic anhydride. In the examples, the following compounds are prepared by the above methods: malonic acid diethyl esters, free acids and dichlorides substituted by [(6-methyl-2 : 5-endomethylene-D 3-cyclohexenyl - methyl)]- and [2 : 5 - endomethylene - D 3 - cyclohexenyl - (1)] - radicals, [3-(21 : 51 - endomethylene - D 31 - cyclohexenyl)-propyl-(1)]-malonic acid diethyl ester and 6-methyl - 2 : 5 - endomethylene - D 3 - cyclo - hexenyl - methyl bromide. 1-Bromobutene-(2) is prepared from butadiene and hydrogen bromide in glacial acetic acid. 3-(21 : 51-Endomethylene - D 3 - cyclohexenyl) - propyl bromide is obtained from PBr3 and the corresponding propanol, itself obtained by converting 2 : 5-endomethylene - D 3 - cyclohexenyl - (1) - methyl bromide into the corresponding Grignard compound and reacting this with ethylene oxide. p.p1 - Dimethyl-, p.p1-dichloro-, m.m1-dibromo- and m.m1 - dimethylmercapto - hydrazo - benzenes are produced by reduction with zinc dust and alkali of p-nitrotoluene, p-nitrochlorobenzene, m-bromonitrobenzene and mi-nitrothioanisole respectively. Specification 646,597 is referred to.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH768813X | 1954-05-07 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB768813A true GB768813A (en) | 1957-02-20 |
Family
ID=4535231
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB12243/55A Expired GB768813A (en) | 1954-05-07 | 1955-04-28 | Substituted 1.2-diphenyl-3.5-dioxo-pyrazolidines and processes for the production thereof |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB768813A (en) |
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB2336843A (en) * | 1998-04-30 | 1999-11-03 | Hyundai Electronics Ind | Carboxyl-containing alicyclic monomers for photoresist resins |
US6291131B1 (en) | 1998-08-26 | 2001-09-18 | Hyundai Electronics Industries Co., Ltd. | Monomers for photoresist, polymers thereof, and photoresist compositions using the same |
US6369181B1 (en) | 1997-12-29 | 2002-04-09 | Hyundai Electronics Industries Co., Ltd. | Copolymer resin, preparation thereof, and photoresist using the same |
US6391518B1 (en) | 1998-07-27 | 2002-05-21 | Hyundai Electronics Industries Co., Ltd. | Polymers and photoresist compositions using the same |
US6410670B1 (en) | 1998-08-26 | 2002-06-25 | Hyundai Electronics Industries Co., Ltd. | Photoresist monomer having hydroxy group and carboxy group, copolymer thereof and photoresist composition using the same |
US6569971B2 (en) | 1998-08-27 | 2003-05-27 | Hyundai Electronics Industries Co., Ltd. | Polymers for photoresist and photoresist compositions using the same |
-
1955
- 1955-04-28 GB GB12243/55A patent/GB768813A/en not_active Expired
Cited By (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6369181B1 (en) | 1997-12-29 | 2002-04-09 | Hyundai Electronics Industries Co., Ltd. | Copolymer resin, preparation thereof, and photoresist using the same |
US6608158B2 (en) | 1997-12-29 | 2003-08-19 | Hyundai Electronics Industries Co., Ltd. | Copolymer resin, preparation thereof, and photoresist using the same |
GB2336843A (en) * | 1998-04-30 | 1999-11-03 | Hyundai Electronics Ind | Carboxyl-containing alicyclic monomers for photoresist resins |
US6265130B1 (en) | 1998-04-30 | 2001-07-24 | Hyundai Electronics Industries Co., Ltd. | Photoresist polymers of carboxyl-containing alicyclic compounds |
US6376632B1 (en) | 1998-04-30 | 2002-04-23 | Hyundai Electronics Industries Co., Ltd. | Photoresist polymers of carboxyl-containing alicyclic compounds |
GB2336843B (en) * | 1998-04-30 | 2003-11-05 | Hyundai Electronics Ind | Carboxyl-containing alicyclic compounds and a process for preparing the same |
US6391518B1 (en) | 1998-07-27 | 2002-05-21 | Hyundai Electronics Industries Co., Ltd. | Polymers and photoresist compositions using the same |
US6291131B1 (en) | 1998-08-26 | 2001-09-18 | Hyundai Electronics Industries Co., Ltd. | Monomers for photoresist, polymers thereof, and photoresist compositions using the same |
US6410670B1 (en) | 1998-08-26 | 2002-06-25 | Hyundai Electronics Industries Co., Ltd. | Photoresist monomer having hydroxy group and carboxy group, copolymer thereof and photoresist composition using the same |
US6586619B2 (en) | 1998-08-26 | 2003-07-01 | Hyundai Electronics Industries Co., Ltd. | Photoresist monomer having hydroxy group and carboxy group, copolymer thereof and photoresist composition using the same |
US6569971B2 (en) | 1998-08-27 | 2003-05-27 | Hyundai Electronics Industries Co., Ltd. | Polymers for photoresist and photoresist compositions using the same |
US6987155B2 (en) | 1998-08-27 | 2006-01-17 | Hyundai Electronics Industries Co., Ltd. | Polymers for photoresist and photoresist compositions using the same |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US2359208A (en) | beta-substituted-delta alpha,beta-gamma-butyrolactones and beta-substituted-beta-hydroxy-gamma-butyrolactones and the methods of preparing them | |
GB768813A (en) | Substituted 1.2-diphenyl-3.5-dioxo-pyrazolidines and processes for the production thereof | |
US2934556A (en) | Boron compounds and methods of preparation | |
US2950328A (en) | Cycopropyl derivatives and processes for making the same | |
US3142692A (en) | Preparation of beta-keto esters | |
US2806874A (en) | Mixed isomeric octen-1-ols and their preparation | |
GB734823A (en) | Improvements in or relating to coumarin derivatives and the process for the manufacture of these derivatives | |
GB669179A (en) | Organo silicon compounds | |
GB820083A (en) | Reactions of organomagnesium chloride reagents | |
GB773022A (en) | Improvements in and relating to 4-substituted 1:2-diaryl-3:5-dioxo-pyrazolidines | |
GB1264892A (en) | ||
GB738839A (en) | New basic esters of phosphorus-containing acids | |
GB854950A (en) | Process for the production of heterocyclic carboxylic acids of the pyrazole series, as well as their esters and salts | |
US2632019A (en) | Alkyl esters of phosphono bis beta cyanoethyl acetic acid and acetic acid nitrile | |
GB1074197A (en) | Preparation of phenoxyacetic acids | |
GB781438A (en) | 4-substituted 1.2-diphenyl-3.5-dioxo-pyrazolidines and process for their production | |
GB885524A (en) | Cyclopentadiene derivatives | |
GB777814A (en) | New malonic, cyanoacetic and acetoacetic acid derivatives, and processes for making and using the same | |
Clemo et al. | 398. The nitration of some derivatives of eugenol | |
GB606192A (en) | Improvements in or relating to thiophene compounds and processes of preparing the same | |
ES308051A1 (en) | Procedure for the elaboration of new carboxylic acid esters, basically substituted. (Machine-translation by Google Translate, not legally binding) | |
GB763440A (en) | Manufacture of organo-mercury compounds suitable as diuretics | |
GB793968A (en) | Process for the production of 4-substituted 1.2-diaryl-3.5-dioxo-pyrazolidines | |
ES366534A1 (en) | 1,2-oxazinyl phenyl alkanoic acids | |
GB785086A (en) | Novel unsaturated ketones and a process for the manufacture thereof |