DE3027845A1 - Verfahren zur herstellung von 3-amino-1-phenylpyrazol-5-on - Google Patents
Verfahren zur herstellung von 3-amino-1-phenylpyrazol-5-onInfo
- Publication number
- DE3027845A1 DE3027845A1 DE19803027845 DE3027845A DE3027845A1 DE 3027845 A1 DE3027845 A1 DE 3027845A1 DE 19803027845 DE19803027845 DE 19803027845 DE 3027845 A DE3027845 A DE 3027845A DE 3027845 A1 DE3027845 A1 DE 3027845A1
- Authority
- DE
- Germany
- Prior art keywords
- phenylhydrazine
- distilled
- reaction
- mol
- alcoholate
- 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.)
- Withdrawn
Links
- PVKNQGWSRAGMNM-UHFFFAOYSA-N 5-amino-2-phenyl-1h-pyrazol-3-one Chemical compound N1C(N)=CC(=O)N1C1=CC=CC=C1 PVKNQGWSRAGMNM-UHFFFAOYSA-N 0.000 title claims description 4
- 238000004519 manufacturing process Methods 0.000 title 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 39
- 238000006243 chemical reaction Methods 0.000 claims description 17
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical group CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 15
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 13
- HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 claims description 13
- 229940067157 phenylhydrazine Drugs 0.000 claims description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 11
- 239000002798 polar solvent Substances 0.000 claims description 5
- 239000011541 reaction mixture Substances 0.000 claims description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 4
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 4
- 150000001298 alcohols Chemical class 0.000 claims description 4
- 150000002148 esters Chemical class 0.000 claims description 4
- ZIUSEGSNTOUIPT-UHFFFAOYSA-N ethyl 2-cyanoacetate Chemical compound CCOC(=O)CC#N ZIUSEGSNTOUIPT-UHFFFAOYSA-N 0.000 claims description 4
- 238000010438 heat treatment Methods 0.000 claims description 4
- 238000001556 precipitation Methods 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 3
- 229910052783 alkali metal Inorganic materials 0.000 claims description 3
- 150000001340 alkali metals Chemical class 0.000 claims description 3
- -1 alkyl cyanoacetate Chemical compound 0.000 claims description 3
- 238000009835 boiling Methods 0.000 claims description 3
- ANGDWNBGPBMQHW-UHFFFAOYSA-N methyl cyanoacetate Chemical compound COC(=O)CC#N ANGDWNBGPBMQHW-UHFFFAOYSA-N 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- 239000003638 chemical reducing agent Substances 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 238000009833 condensation Methods 0.000 claims description 2
- 230000005494 condensation Effects 0.000 claims description 2
- 125000003158 alcohol group Chemical group 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- MLIREBYILWEBDM-UHFFFAOYSA-N cyanoacetic acid Chemical compound OC(=O)CC#N MLIREBYILWEBDM-UHFFFAOYSA-N 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000010626 work up procedure Methods 0.000 description 2
- MLIREBYILWEBDM-UHFFFAOYSA-M 2-cyanoacetate Chemical compound [O-]C(=O)CC#N MLIREBYILWEBDM-UHFFFAOYSA-M 0.000 description 1
- 241000638584 Cethosia cyane Species 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910052977 alkali metal sulfide Inorganic materials 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- WBZKQQHYRPRKNJ-UHFFFAOYSA-L disulfite Chemical compound [O-]S(=O)S([O-])(=O)=O WBZKQQHYRPRKNJ-UHFFFAOYSA-L 0.000 description 1
- GRWZHXKQBITJKP-UHFFFAOYSA-L dithionite(2-) Chemical compound [O-]S(=O)S([O-])=O GRWZHXKQBITJKP-UHFFFAOYSA-L 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000004809 thin layer chromatography Methods 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
- C07D231/44—Oxygen and nitrogen or sulfur and nitrogen atoms
- C07D231/52—Oxygen atom in position 3 and nitrogen atom in position 5, or vice versa
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19803027845 DE3027845A1 (de) | 1980-07-23 | 1980-07-23 | Verfahren zur herstellung von 3-amino-1-phenylpyrazol-5-on |
| DE8181105597T DE3162031D1 (en) | 1980-07-23 | 1981-07-16 | Process for the preparation of 3-amino-1-phenyl-pyrazol-5-one |
| EP81105597A EP0045414B1 (de) | 1980-07-23 | 1981-07-16 | Verfahren zur Herstellung von 3-Amino-1-phenylpyrazol-5-on |
| US06/285,469 US4410707A (en) | 1980-07-23 | 1981-07-21 | Process for the manufacture of 3-amino-1-phenylpyrazol-5-one |
| JP56113780A JPS5756462A (en) | 1980-07-23 | 1981-07-22 | Manufacture of 3-amino-1-phenylpyrazol-5-one |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19803027845 DE3027845A1 (de) | 1980-07-23 | 1980-07-23 | Verfahren zur herstellung von 3-amino-1-phenylpyrazol-5-on |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE3027845A1 true DE3027845A1 (de) | 1982-02-25 |
Family
ID=6107885
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19803027845 Withdrawn DE3027845A1 (de) | 1980-07-23 | 1980-07-23 | Verfahren zur herstellung von 3-amino-1-phenylpyrazol-5-on |
| DE8181105597T Expired DE3162031D1 (en) | 1980-07-23 | 1981-07-16 | Process for the preparation of 3-amino-1-phenyl-pyrazol-5-one |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE8181105597T Expired DE3162031D1 (en) | 1980-07-23 | 1981-07-16 | Process for the preparation of 3-amino-1-phenyl-pyrazol-5-one |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US4410707A (enExample) |
| EP (1) | EP0045414B1 (enExample) |
| JP (1) | JPS5756462A (enExample) |
| DE (2) | DE3027845A1 (enExample) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4786725A (en) * | 1982-06-28 | 1988-11-22 | Engelhard Corporation | Solubilized platinum (II) complexes |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1558513A (enExample) * | 1968-01-04 | 1969-02-28 | ||
| FR1599034A (enExample) * | 1968-11-07 | 1970-07-15 | ||
| FR2044125A6 (en) * | 1969-05-09 | 1971-02-19 | Roussel Uclaf | 1-(3'-trifluoromethylphenyl)-3-amino-4,4- - dichloro-5-pyrazolone useful as an anti- |
| FR2130941A5 (en) * | 1971-03-26 | 1972-11-10 | Roussel Uclaf | Pyrazolinones ,pyridazinone and diazepinone derivs - - useful as pesticides |
-
1980
- 1980-07-23 DE DE19803027845 patent/DE3027845A1/de not_active Withdrawn
-
1981
- 1981-07-16 EP EP81105597A patent/EP0045414B1/de not_active Expired
- 1981-07-16 DE DE8181105597T patent/DE3162031D1/de not_active Expired
- 1981-07-21 US US06/285,469 patent/US4410707A/en not_active Expired - Fee Related
- 1981-07-22 JP JP56113780A patent/JPS5756462A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| DE3162031D1 (en) | 1984-03-01 |
| EP0045414A2 (de) | 1982-02-10 |
| EP0045414B1 (de) | 1984-01-25 |
| US4410707A (en) | 1983-10-18 |
| JPS5756462A (en) | 1982-04-05 |
| JPH038344B2 (enExample) | 1991-02-05 |
| EP0045414A3 (en) | 1982-02-24 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8130 | Withdrawal |