SU535907A3 - Способ получени 1-(4-метил-6окси-2-пиримидинил)-3-метилпиразолин-5-она - Google Patents
Способ получени 1-(4-метил-6окси-2-пиримидинил)-3-метилпиразолин-5-онаInfo
- Publication number
- SU535907A3 SU535907A3 SU1814751A SU1814751A SU535907A3 SU 535907 A3 SU535907 A3 SU 535907A3 SU 1814751 A SU1814751 A SU 1814751A SU 1814751 A SU1814751 A SU 1814751A SU 535907 A3 SU535907 A3 SU 535907A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- methyl
- solution
- reaction
- water
- methylpyrazolin
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 15
- 239000000243 solution Substances 0.000 claims 12
- 238000006243 chemical reaction Methods 0.000 claims 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 6
- 239000003054 catalyst Substances 0.000 claims 6
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 4
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims 4
- -1 methyl acetoacetic ester Chemical compound 0.000 claims 4
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 claims 4
- FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 claims 3
- 239000007864 aqueous solution Substances 0.000 claims 3
- 238000001816 cooling Methods 0.000 claims 3
- 238000000354 decomposition reaction Methods 0.000 claims 3
- 239000013067 intermediate product Substances 0.000 claims 3
- 239000002244 precipitate Substances 0.000 claims 3
- 239000002904 solvent Substances 0.000 claims 3
- WDJHALXBUFZDSR-UHFFFAOYSA-N Acetoacetic acid Natural products CC(=O)CC(O)=O WDJHALXBUFZDSR-UHFFFAOYSA-N 0.000 claims 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims 2
- RHAXSHUQNIEUEY-UHFFFAOYSA-N Epirizole Chemical compound COC1=CC(C)=NN1C1=NC(C)=CC(OC)=N1 RHAXSHUQNIEUEY-UHFFFAOYSA-N 0.000 claims 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 2
- GCPWJFKTWGFEHH-UHFFFAOYSA-N acetoacetamide Chemical compound CC(=O)CC(N)=O GCPWJFKTWGFEHH-UHFFFAOYSA-N 0.000 claims 2
- 239000003513 alkali Substances 0.000 claims 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims 2
- HAMNKKUPIHEESI-UHFFFAOYSA-N aminoguanidine Chemical compound NNC(N)=N HAMNKKUPIHEESI-UHFFFAOYSA-N 0.000 claims 2
- 235000011114 ammonium hydroxide Nutrition 0.000 claims 2
- 150000004649 carbonic acid derivatives Chemical class 0.000 claims 2
- WOWBFOBYOAGEEA-UHFFFAOYSA-N diafenthiuron Chemical compound CC(C)C1=C(NC(=S)NC(C)(C)C)C(C(C)C)=CC(OC=2C=CC=CC=2)=C1 WOWBFOBYOAGEEA-UHFFFAOYSA-N 0.000 claims 2
- 150000004679 hydroxides Chemical class 0.000 claims 2
- 239000012442 inert solvent Substances 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- 150000007530 organic bases Chemical class 0.000 claims 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- OTXHZHQQWQTQMW-UHFFFAOYSA-N (diaminomethylideneamino)azanium;hydrogen carbonate Chemical compound OC([O-])=O.N[NH2+]C(N)=N OTXHZHQQWQTQMW-UHFFFAOYSA-N 0.000 claims 1
- FUSNOPLQVRUIIM-UHFFFAOYSA-N 4-amino-2-(4,4-dimethyl-2-oxoimidazolidin-1-yl)-n-[3-(trifluoromethyl)phenyl]pyrimidine-5-carboxamide Chemical compound O=C1NC(C)(C)CN1C(N=C1N)=NC=C1C(=O)NC1=CC=CC(C(F)(F)F)=C1 FUSNOPLQVRUIIM-UHFFFAOYSA-N 0.000 claims 1
- STYNLVLGNUXNJE-UHFFFAOYSA-N 5-methyl-2,3-dihydro-1h-pyrazole Chemical compound CC1=CCNN1 STYNLVLGNUXNJE-UHFFFAOYSA-N 0.000 claims 1
- ZWPLPUGPPROJDJ-UHFFFAOYSA-N 6-methyl-2-(5-methyl-3-oxo-1h-pyrazol-2-yl)-1h-pyrimidin-4-one Chemical compound N1C(C)=CC(=O)N1C1=NC(=O)C=C(C)N1 ZWPLPUGPPROJDJ-UHFFFAOYSA-N 0.000 claims 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 claims 1
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 claims 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims 1
- 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 claims 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims 1
- 150000001342 alkaline earth metals Chemical class 0.000 claims 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims 1
- 150000001408 amides Chemical class 0.000 claims 1
- 229910021529 ammonia Inorganic materials 0.000 claims 1
- 239000003153 chemical reaction reagent Substances 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 claims 1
- 239000013078 crystal Substances 0.000 claims 1
- WASQWSOJHCZDFK-UHFFFAOYSA-N diketene Chemical compound C=C1CC(=O)O1 WASQWSOJHCZDFK-UHFFFAOYSA-N 0.000 claims 1
- 125000005594 diketone group Chemical group 0.000 claims 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 claims 1
- 238000010828 elution Methods 0.000 claims 1
- 238000010438 heat treatment Methods 0.000 claims 1
- 239000012493 hydrazine sulfate Substances 0.000 claims 1
- 229910000377 hydrazine sulfate Inorganic materials 0.000 claims 1
- 150000007529 inorganic bases Chemical class 0.000 claims 1
- 238000002844 melting Methods 0.000 claims 1
- 230000008018 melting Effects 0.000 claims 1
- 229910000027 potassium carbonate Inorganic materials 0.000 claims 1
- 239000000047 product Substances 0.000 claims 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 1
- 239000011541 reaction mixture Substances 0.000 claims 1
- 238000001953 recrystallisation Methods 0.000 claims 1
- 238000010992 reflux Methods 0.000 claims 1
- 229910052708 sodium Inorganic materials 0.000 claims 1
- 239000011734 sodium Substances 0.000 claims 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
- C07D231/18—One oxygen or sulfur atom
- C07D231/20—One oxygen atom attached in position 3 or 5
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5767571A JPS553351B1 (enExample) | 1971-07-31 | 1971-07-31 | |
| JP5921671A JPS558509B2 (enExample) | 1971-08-05 | 1971-08-05 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU535907A3 true SU535907A3 (ru) | 1976-11-15 |
Family
ID=26398738
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU1814751A SU535907A3 (ru) | 1971-07-31 | 1972-07-28 | Способ получени 1-(4-метил-6окси-2-пиримидинил)-3-метилпиразолин-5-она |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US3865825A (enExample) |
| AT (1) | AT323178B (enExample) |
| BG (1) | BG20358A3 (enExample) |
| DE (1) | DE2237632C3 (enExample) |
| DK (1) | DK135993B (enExample) |
| ES (1) | ES405276A1 (enExample) |
| FI (1) | FI55840C (enExample) |
| IL (1) | IL40006A (enExample) |
| NO (1) | NO138408C (enExample) |
| SU (1) | SU535907A3 (enExample) |
| YU (1) | YU35128B (enExample) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20090114634A1 (en) * | 2005-02-17 | 2009-05-07 | David Naylor | Heating unit for warming fluid conduits |
| US10920379B2 (en) | 2005-02-17 | 2021-02-16 | Greenheat Ip Holdings Llc | Grounded modular heated cover |
| US20090302023A1 (en) * | 2008-05-12 | 2009-12-10 | Thomas Caterina | Heating unit for warming pallets of materials |
| US20090107975A1 (en) * | 2005-02-17 | 2009-04-30 | Thomas Caterina | Heating unit for warming pallets |
| US20090107972A1 (en) * | 2005-02-17 | 2009-04-30 | David Naylor | Heating unit for warming propane tanks |
| US8633425B2 (en) * | 2005-02-17 | 2014-01-21 | 417 And 7/8, Llc | Systems, methods, and devices for storing, heating, and dispensing fluid |
| US9945080B2 (en) * | 2005-02-17 | 2018-04-17 | Greenheat Ip Holdings, Llc | Grounded modular heated cover |
| US20090101632A1 (en) | 2005-02-17 | 2009-04-23 | David Naylor | Heating unit for direct current applications |
| US20090114633A1 (en) * | 2005-02-17 | 2009-05-07 | David Naylor | Portable Pouch Heating Unit |
| US20090107986A1 (en) * | 2005-02-17 | 2009-04-30 | David Naylor | Three layer glued laminate heating unit |
| US8258443B2 (en) * | 2005-02-17 | 2012-09-04 | 417 And 7/8, Llc | Heating unit for warming pallets |
| US8592582B2 (en) | 2010-01-18 | 2013-11-26 | Shiseido Company, Ltd. | Method for producing pyrimidinylpyrazole compounds |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2731473A (en) * | 1956-01-17 | New pyrazolone derivatives |
-
1972
- 1972-07-18 BG BG020992A patent/BG20358A3/xx unknown
- 1972-07-25 FI FI2082/72A patent/FI55840C/fi active
- 1972-07-26 IL IL40006A patent/IL40006A/en unknown
- 1972-07-28 NO NO2714/72A patent/NO138408C/no unknown
- 1972-07-28 YU YU1960/72A patent/YU35128B/xx unknown
- 1972-07-28 DK DK376172AA patent/DK135993B/da unknown
- 1972-07-28 AT AT653572A patent/AT323178B/de not_active IP Right Cessation
- 1972-07-28 SU SU1814751A patent/SU535907A3/ru active
- 1972-07-28 ES ES405276A patent/ES405276A1/es not_active Expired
- 1972-07-31 DE DE2237632A patent/DE2237632C3/de not_active Expired
- 1972-07-31 US US276469A patent/US3865825A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| ES405276A1 (es) | 1975-07-01 |
| DE2237632A1 (de) | 1973-02-15 |
| AT323178B (de) | 1975-06-25 |
| US3865825A (en) | 1975-02-11 |
| NO138408B (no) | 1978-05-22 |
| FI55840C (fi) | 1979-10-10 |
| DE2237632B2 (de) | 1979-07-05 |
| NO138408C (no) | 1978-08-30 |
| YU196072A (en) | 1979-12-31 |
| IL40006A0 (en) | 1972-09-28 |
| DK135993B (da) | 1977-07-25 |
| DK135993C (enExample) | 1977-12-27 |
| FI55840B (fi) | 1979-06-29 |
| YU35128B (en) | 1980-09-25 |
| IL40006A (en) | 1976-06-30 |
| BG20358A3 (bg) | 1975-11-05 |
| DE2237632C3 (de) | 1980-03-06 |
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