JPS6227068B2 - - Google Patents
Info
- Publication number
- JPS6227068B2 JPS6227068B2 JP60036705A JP3670585A JPS6227068B2 JP S6227068 B2 JPS6227068 B2 JP S6227068B2 JP 60036705 A JP60036705 A JP 60036705A JP 3670585 A JP3670585 A JP 3670585A JP S6227068 B2 JPS6227068 B2 JP S6227068B2
- Authority
- JP
- Japan
- Prior art keywords
- palladium
- diphenyl
- diphenylpyrazole
- parts
- reference example
- 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
- 239000003054 catalyst Substances 0.000 claims description 19
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 15
- JXHKUYQCEJILEI-UHFFFAOYSA-N 3,5-diphenyl-1h-pyrazole Chemical compound C=1C(C=2C=CC=CC=2)=NNC=1C1=CC=CC=C1 JXHKUYQCEJILEI-UHFFFAOYSA-N 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 14
- 238000010992 reflux Methods 0.000 claims description 14
- 239000002904 solvent Substances 0.000 claims description 6
- RXQQWLMUBOTBSO-UHFFFAOYSA-N 3,5-diphenyl-2,3-dihydro-1h-pyrazole Chemical compound N1NC(C=2C=CC=CC=2)=CC1C1=CC=CC=C1 RXQQWLMUBOTBSO-UHFFFAOYSA-N 0.000 claims description 5
- DSVGQVZAZSZEEX-UHFFFAOYSA-N [C].[Pt] Chemical compound [C].[Pt] DSVGQVZAZSZEEX-UHFFFAOYSA-N 0.000 claims description 4
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 4
- 229910052763 palladium Inorganic materials 0.000 claims description 4
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Inorganic materials [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 claims description 3
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 239000007858 starting material Substances 0.000 claims description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
- 239000012442 inert solvent Substances 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 7
- VJFQJTFADLQQNS-UHFFFAOYSA-N 3,5-diphenyl-4,5-dihydro-1h-pyrazole Chemical compound C1C(C=2C=CC=CC=2)NN=C1C1=CC=CC=C1 VJFQJTFADLQQNS-UHFFFAOYSA-N 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 6
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- GODJIHYACPNRIJ-UHFFFAOYSA-N 4-methyl-3,5-diphenyl-1h-pyrazole Chemical compound CC=1C(C=2C=CC=CC=2)=NNC=1C1=CC=CC=C1 GODJIHYACPNRIJ-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
- 239000008096 xylene Substances 0.000 description 4
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 238000006356 dehydrogenation reaction Methods 0.000 description 3
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- DQFBYFPFKXHELB-VAWYXSNFSA-N trans-chalcone Chemical compound C=1C=CC=CC=1C(=O)\C=C\C1=CC=CC=C1 DQFBYFPFKXHELB-VAWYXSNFSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical group CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- XOFYZVNMUHMLCC-ZPOLXVRWSA-N prednisone Chemical compound O=C1C=C[C@]2(C)[C@H]3C(=O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 XOFYZVNMUHMLCC-ZPOLXVRWSA-N 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- GIWVQKNTAVVGBQ-UHFFFAOYSA-N 4-methyl-3,5-diphenyl-2,3-dihydro-1h-pyrazole Chemical compound CC1=C(C=2C=CC=CC=2)NNC1C1=CC=CC=C1 GIWVQKNTAVVGBQ-UHFFFAOYSA-N 0.000 description 1
- DQFBYFPFKXHELB-UHFFFAOYSA-N Chalcone Natural products C=1C=CC=CC=1C(=O)C=CC1=CC=CC=C1 DQFBYFPFKXHELB-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- -1 alkyl chalcone Chemical compound 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- FFSAXUULYPJSKH-UHFFFAOYSA-N butyrophenone Chemical group CCCC(=O)C1=CC=CC=C1 FFSAXUULYPJSKH-UHFFFAOYSA-N 0.000 description 1
- 235000005513 chalcones Nutrition 0.000 description 1
- 229960004285 fomepizole Drugs 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- KRIOVPPHQSLHCZ-UHFFFAOYSA-N propiophenone Chemical compound CCC(=O)C1=CC=CC=C1 KRIOVPPHQSLHCZ-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation 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
- C07D231/06—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
-
- 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
- C07D231/12—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 only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19853522542 DE3522542A1 (de) | 1985-02-27 | 1985-06-24 | Wegwerf-schneideinsatz |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/549,219 US3952010A (en) | 1973-09-17 | 1975-02-12 | Catalytic dehydrogenation process for the preparation of 3,5-disubstituted pyrazoles |
| US549219 | 1983-11-07 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS60222463A JPS60222463A (ja) | 1985-11-07 |
| JPS6227068B2 true JPS6227068B2 (ru) | 1987-06-12 |
Family
ID=24192112
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP51012890A Pending JPS51101979A (ru) | 1975-02-12 | 1976-02-10 | |
| JP60036705A Granted JPS60222463A (ja) | 1975-02-12 | 1985-02-27 | ３，５−ジフエニルピラゾ−ル類の製法 |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP51012890A Pending JPS51101979A (ru) | 1975-02-12 | 1976-02-10 |
Country Status (19)
| Country | Link |
|---|---|
| JP (2) | JPS51101979A (ru) |
| AT (1) | AT350549B (ru) |
| BE (1) | BE838408R (ru) |
| BR (1) | BR7600847A (ru) |
| CA (1) | CA1060455A (ru) |
| CH (1) | CH608004A5 (ru) |
| CS (1) | CS192554B2 (ru) |
| DD (1) | DD124249A6 (ru) |
| DE (1) | DE2602965A1 (ru) |
| DK (1) | DK55276A (ru) |
| ES (1) | ES445094A2 (ru) |
| FR (1) | FR2300763A2 (ru) |
| GB (1) | GB1537859A (ru) |
| IL (1) | IL48724A (ru) |
| IT (1) | IT1053296B (ru) |
| NL (1) | NL178075C (ru) |
| SE (1) | SE7601544L (ru) |
| SU (1) | SU799657A3 (ru) |
| ZA (1) | ZA757986B (ru) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3029160A1 (de) * | 1980-08-01 | 1982-03-04 | Basf Ag, 6700 Ludwigshafen | Verfahren zur herstellung von pyrazolen |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5855148A (ja) * | 1981-09-29 | 1983-04-01 | Hino Motors Ltd | 成形用金型の製造方法 |
-
1975
- 1975-12-22 CA CA242,256A patent/CA1060455A/en not_active Expired
- 1975-12-23 ZA ZA00757986A patent/ZA757986B/xx unknown
- 1975-12-24 IL IL48724A patent/IL48724A/xx unknown
-
1976
- 1976-01-09 IT IT47573/76A patent/IT1053296B/it active
- 1976-01-16 NL NLAANVRAGE7600445,A patent/NL178075C/xx not_active IP Right Cessation
- 1976-01-27 DE DE19762602965 patent/DE2602965A1/de active Granted
- 1976-02-03 DD DD191069A patent/DD124249A6/xx unknown
- 1976-02-10 JP JP51012890A patent/JPS51101979A/ja active Pending
- 1976-02-10 BE BE164196A patent/BE838408R/xx not_active IP Right Cessation
- 1976-02-10 FR FR7603642A patent/FR2300763A2/fr active Granted
- 1976-02-11 SE SE7601544A patent/SE7601544L/xx unknown
- 1976-02-11 DK DK55276*#A patent/DK55276A/da unknown
- 1976-02-11 CS CS76899A patent/CS192554B2/cs unknown
- 1976-02-11 SU SU762319859A patent/SU799657A3/ru active
- 1976-02-11 CH CH166976A patent/CH608004A5/xx not_active IP Right Cessation
- 1976-02-11 AT AT96276A patent/AT350549B/de not_active IP Right Cessation
- 1976-02-11 BR BR7600847A patent/BR7600847A/pt unknown
- 1976-02-12 ES ES445094A patent/ES445094A2/es not_active Expired
- 1976-02-12 GB GB5650/76A patent/GB1537859A/en not_active Expired
-
1985
- 1985-02-27 JP JP60036705A patent/JPS60222463A/ja active Granted
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5855148A (ja) * | 1981-09-29 | 1983-04-01 | Hino Motors Ltd | 成形用金型の製造方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| DD124249A6 (ru) | 1977-02-09 |
| CS192554B2 (en) | 1979-08-31 |
| SU799657A3 (ru) | 1981-01-23 |
| BE838408R (fr) | 1976-08-10 |
| FR2300763A2 (fr) | 1976-09-10 |
| DK55276A (da) | 1976-08-13 |
| IL48724A (en) | 1979-07-25 |
| FR2300763B2 (ru) | 1982-09-03 |
| GB1537859A (en) | 1979-01-04 |
| BR7600847A (pt) | 1976-09-14 |
| NL178075C (nl) | 1986-01-16 |
| ZA757986B (en) | 1976-12-29 |
| AT350549B (de) | 1979-06-11 |
| CH608004A5 (en) | 1978-12-15 |
| IT1053296B (it) | 1981-08-31 |
| NL7600445A (nl) | 1976-08-16 |
| SE7601544L (sv) | 1976-08-13 |
| DE2602965C2 (ru) | 1988-11-17 |
| AU8790475A (en) | 1977-06-30 |
| ES445094A2 (es) | 1977-06-16 |
| DE2602965A1 (de) | 1976-08-26 |
| IL48724A0 (en) | 1976-02-29 |
| CA1060455A (en) | 1979-08-14 |
| ATA96276A (de) | 1978-11-15 |
| JPS51101979A (ru) | 1976-09-08 |
| JPS60222463A (ja) | 1985-11-07 |
| NL178075B (nl) | 1985-08-16 |
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