DE1620408A1 - Verfahren zur Herstellung von 1,2-Diaryl-3,5-dioxopyrazolidinen - Google Patents
Verfahren zur Herstellung von 1,2-Diaryl-3,5-dioxopyrazolidinenInfo
- Publication number
- DE1620408A1 DE1620408A1 DE19661620408 DE1620408A DE1620408A1 DE 1620408 A1 DE1620408 A1 DE 1620408A1 DE 19661620408 DE19661620408 DE 19661620408 DE 1620408 A DE1620408 A DE 1620408A DE 1620408 A1 DE1620408 A1 DE 1620408A1
- Authority
- DE
- Germany
- Prior art keywords
- diaryl
- general formula
- dioxopyrazolidines
- formula
- iii
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 239000013067 intermediate product Substances 0.000 claims description 3
- 229910052744 lithium Inorganic materials 0.000 claims description 3
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 150000002641 lithium Chemical group 0.000 claims description 2
- 125000002524 organometallic group Chemical group 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- USPWKWBDZOARPV-UHFFFAOYSA-N pyrazolidine Chemical compound C1CNNC1 USPWKWBDZOARPV-UHFFFAOYSA-N 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- -1 phenyl radicals Chemical class 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 2
- FUSUHKVFWTUUBE-UHFFFAOYSA-N buten-2-one Chemical compound CC(=O)C=C FUSUHKVFWTUUBE-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- MEOXDUFIBPDSFD-UHFFFAOYSA-N C1(=CC=CC=C1)N1N(C(C(C1=O)CCC#N)=O)C1=CC=CC=C1 Chemical compound C1(=CC=CC=C1)N1N(C(C(C1=O)CCC#N)=O)C1=CC=CC=C1 MEOXDUFIBPDSFD-UHFFFAOYSA-N 0.000 description 1
- 239000007818 Grignard reagent Substances 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 238000007011 Robinson annulation reaction Methods 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 230000006203 ethylation Effects 0.000 description 1
- 238000006200 ethylation reaction Methods 0.000 description 1
- 150000004795 grignard reagents Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- VXWPONVCMVLXBW-UHFFFAOYSA-M magnesium;carbanide;iodide Chemical compound [CH3-].[Mg+2].[I-] VXWPONVCMVLXBW-UHFFFAOYSA-M 0.000 description 1
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- VYMDGNCVAMGZFE-UHFFFAOYSA-N phenylbutazonum Chemical compound O=C1C(CCCC)C(=O)N(C=2C=CC=CC=2)N1C1=CC=CC=C1 VYMDGNCVAMGZFE-UHFFFAOYSA-N 0.000 description 1
- NHKJPPKXDNZFBJ-UHFFFAOYSA-N phenyllithium Chemical compound [Li]C1=CC=CC=C1 NHKJPPKXDNZFBJ-UHFFFAOYSA-N 0.000 description 1
- ANRQGKOBLBYXFM-UHFFFAOYSA-M phenylmagnesium bromide Chemical compound Br[Mg]C1=CC=CC=C1 ANRQGKOBLBYXFM-UHFFFAOYSA-M 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- DNTVKOMHCDKATN-UHFFFAOYSA-N pyrazolidine-3,5-dione Chemical class O=C1CC(=O)NN1 DNTVKOMHCDKATN-UHFFFAOYSA-N 0.000 description 1
- 150000003839 salts Chemical group 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Classifications
-
- 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
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D231/28—Two oxygen or sulfur atoms
- C07D231/30—Two oxygen or sulfur atoms attached in positions 3 and 5
- C07D231/32—Oxygen atoms
- C07D231/36—Oxygen atoms with hydrocarbon radicals, substituted by hetero atoms, attached in position 4
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Epoxy Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS580665 | 1965-09-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1620408A1 true DE1620408A1 (de) | 1970-05-14 |
Family
ID=5403639
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19661620408 Pending DE1620408A1 (de) | 1965-09-24 | 1966-09-22 | Verfahren zur Herstellung von 1,2-Diaryl-3,5-dioxopyrazolidinen |
Country Status (11)
| Country | Link |
|---|---|
| AT (1) | AT258897B (enExample) |
| BE (1) | BE687146A (enExample) |
| CH (1) | CH461512A (enExample) |
| DE (1) | DE1620408A1 (enExample) |
| DK (1) | DK114483B (enExample) |
| ES (1) | ES331533A1 (enExample) |
| FI (1) | FI46508C (enExample) |
| GB (1) | GB1098160A (enExample) |
| NL (1) | NL6613352A (enExample) |
| NO (1) | NO122880B (enExample) |
| SE (1) | SE314377B (enExample) |
-
1966
- 1966-09-20 NO NO16479066A patent/NO122880B/no unknown
- 1966-09-20 BE BE687146D patent/BE687146A/xx unknown
- 1966-09-20 CH CH1352666A patent/CH461512A/de unknown
- 1966-09-21 AT AT886566A patent/AT258897B/de active
- 1966-09-21 FI FI247666A patent/FI46508C/fi active
- 1966-09-21 NL NL6613352A patent/NL6613352A/xx unknown
- 1966-09-22 DE DE19661620408 patent/DE1620408A1/de active Pending
- 1966-09-22 SE SE1277066A patent/SE314377B/xx unknown
- 1966-09-23 ES ES0331533A patent/ES331533A1/es not_active Expired
- 1966-09-23 GB GB4244666A patent/GB1098160A/en not_active Expired
- 1966-09-26 DK DK499266A patent/DK114483B/da unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DK114483B (da) | 1969-07-07 |
| FI46508C (fi) | 1973-04-10 |
| NO122880B (enExample) | 1971-08-30 |
| SE314377B (enExample) | 1969-09-08 |
| BE687146A (enExample) | 1967-03-01 |
| GB1098160A (en) | 1968-01-10 |
| FI46508B (fi) | 1973-01-02 |
| NL6613352A (enExample) | 1967-03-28 |
| ES331533A1 (es) | 1967-10-01 |
| CH461512A (de) | 1968-08-31 |
| AT258897B (de) | 1967-12-11 |
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