DE2050234A1 - Arylsulfonylpyrazolverbindungen und Verfahren fur die Herstellung derselben - Google Patents
Arylsulfonylpyrazolverbindungen und Verfahren fur die Herstellung derselbenInfo
- Publication number
- DE2050234A1 DE2050234A1 DE19702050234 DE2050234A DE2050234A1 DE 2050234 A1 DE2050234 A1 DE 2050234A1 DE 19702050234 DE19702050234 DE 19702050234 DE 2050234 A DE2050234 A DE 2050234A DE 2050234 A1 DE2050234 A1 DE 2050234A1
- Authority
- DE
- Germany
- Prior art keywords
- reaction
- formula
- compound
- diazomethane
- carried out
- 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 13
- 150000001875 compounds Chemical class 0.000 title claims description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 22
- 238000006243 chemical reaction Methods 0.000 claims description 16
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 claims description 14
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 239000003960 organic solvent Substances 0.000 claims description 3
- 239000007858 starting material Substances 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims 2
- GVBIARVOCYTPIU-UHFFFAOYSA-N 4-(3-methoxyphenyl)-5-(4-methylphenyl)sulfonyl-1H-pyrazole Chemical compound C1(=CC=C(C=C1)S(=O)(=O)C1=NNC=C1C1=CC(=CC=C1)OC)C GVBIARVOCYTPIU-UHFFFAOYSA-N 0.000 claims 1
- LLHAWJMOGNLAGT-UHFFFAOYSA-N 4-(4-bromophenyl)-5-(4-methylphenyl)sulfonyl-1H-pyrazole Chemical compound C1(=CC=C(C=C1)S(=O)(=O)C1=NNC=C1C1=CC=C(C=C1)Br)C LLHAWJMOGNLAGT-UHFFFAOYSA-N 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
- -1 η-butyl Chemical group 0.000 description 14
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 239000000047 product Substances 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 6
- 239000010410 layer Substances 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 238000004458 analytical method Methods 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000000155 melt Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 150000003217 pyrazoles Chemical class 0.000 description 2
- 239000004332 silver Substances 0.000 description 2
- 229910052709 silver Inorganic materials 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- NPQPATGIGBKPHB-UHFFFAOYSA-N 5-(benzenesulfonyl)-1h-pyrazole Chemical class C=1C=CC=CC=1S(=O)(=O)C=1C=CNN=1 NPQPATGIGBKPHB-UHFFFAOYSA-N 0.000 description 1
- OMIHGPLIXGGMJB-UHFFFAOYSA-N 7-oxabicyclo[4.1.0]hepta-1,3,5-triene Chemical compound C1=CC=C2OC2=C1 OMIHGPLIXGGMJB-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000004799 bromophenyl group Chemical group 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 125000004115 pentoxy group Chemical group [*]OC([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- UEXCJVNBTNXOEH-UHFFFAOYSA-N phenyl acethylene Natural products C#CC1=CC=CC=C1 UEXCJVNBTNXOEH-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000011241 protective layer Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 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
- C07D231/18—One oxygen or sulfur atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP44079073A JPS4832112B1 (enExample) | 1969-10-03 | 1969-10-03 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2050234A1 true DE2050234A1 (de) | 1971-04-15 |
Family
ID=13679696
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19702050234 Pending DE2050234A1 (de) | 1969-10-03 | 1970-10-02 | Arylsulfonylpyrazolverbindungen und Verfahren fur die Herstellung derselben |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US3700688A (enExample) |
| JP (1) | JPS4832112B1 (enExample) |
| DE (1) | DE2050234A1 (enExample) |
| GB (1) | GB1275365A (enExample) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2460299A1 (fr) * | 1979-07-05 | 1981-01-23 | Bellon Labor Sa Roger | Nouveaux derives du pyrazole et leur application therapeutique |
| JPS6147683U (ja) * | 1984-08-30 | 1986-03-31 | 株式会社 イシツカ | 書類ホルダ− |
-
1969
- 1969-10-03 JP JP44079073A patent/JPS4832112B1/ja active Pending
-
1970
- 1970-10-01 US US77347A patent/US3700688A/en not_active Expired - Lifetime
- 1970-10-02 DE DE19702050234 patent/DE2050234A1/de active Pending
- 1970-10-05 GB GB47331/70A patent/GB1275365A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| JPS4832112B1 (enExample) | 1973-10-04 |
| US3700688A (en) | 1972-10-24 |
| GB1275365A (en) | 1972-05-24 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2604119A1 (de) | Neue organische verbindungen und verfahren zu deren herstellung | |
| DE2147023A1 (de) | Verfahren zur herstellung von 1htetrazol-verbindungen | |
| DD202022A5 (de) | Verfahren zur sulfenylierung von n-alkylcarbamaten | |
| EP0710642A2 (de) | Halogenketone | |
| DE2050234A1 (de) | Arylsulfonylpyrazolverbindungen und Verfahren fur die Herstellung derselben | |
| DE1137733B (de) | Verfahren zur Herstellung von Aryl- und Thienylmethylphenylalkylaminen | |
| DE2844394A1 (de) | Neue 4-chloroxazole und verfahren zu deren herstellung | |
| DE2241680C2 (de) | 17-Hydroxy-7-alkoxycarbonyl-3-oxo-17α-pregn-4-en-21-carbonsäure-γ-Lactone und Verfahren und Zwischenprodukte zu ihrer Herstellung | |
| CH617205A5 (enExample) | ||
| CH636103A5 (de) | Verfahren zum herstellen von auranofin. | |
| EP0008333A1 (de) | Alpha-Prop-1-inyl-3-phenoxybenzylalkohole, ihre Herstellung und Verwendung als Zwischenprodukte zur Herstellung von Schädlingsbekämpfungsmitteln | |
| DE3139984A1 (de) | Verfahren zur herstellung von acylphosphinoxiden | |
| DD260493A5 (de) | Verfahren zur herstellung von alkylsulfonylalkychlorbenzolen | |
| EP0360293B1 (de) | Verfahren zur Herstellung von 4,5,6,7-Tetrahydrothieno-[3,2-c]-Pyridinen | |
| DE69118175T2 (de) | Neues disulfidderivat | |
| DE3236096A1 (de) | In der 7- oder 8-stellung chlor- oder trifluormethylsubstituierte n-(chinol-4-yl)-anthranilsaeureester, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel | |
| DE69817120T2 (de) | Verfahren zur herstellung optisch aktiver isomere von trizyklischen verbindungen | |
| DE3026602A1 (de) | 14-oxo-15-halogen-e-homoeburnanderivate, verfahren zur herstellung derselben und von 14-oxo-15-hydroxyimino-e-homoeburnanderivaten und die ersteren enthaltende arzneimittel | |
| EP0311086A1 (de) | N-fluorierte Sulfonamide, Verfahren zu deren Herstellung und deren Verwendung | |
| CH646968A5 (de) | 1,4-dioxaspiro(4,5)decen-verbindungen sowie verfahren zur herstellung von 2-hydroxy-3-substituierten propylarylaethern. | |
| DE2143989A1 (de) | Verfahren zur herstellung von 2-methyl-pyridin-3-ol-derivaten | |
| EP0153656A1 (de) | Verfahren zur Herstellung von 2,6-Dichlorbenzoxazol | |
| EP0421225A2 (de) | Verfahren zur Herstellung von alpha-Chlor-phosphoryliden | |
| DE1695212B2 (de) | Verfahren zur Herstellung von Iodininderivaten | |
| DE3018847A1 (de) | 6- alpha - und 6- beta -substituierte penicillansaeurederivate und verfahren zu ihrer herstellung |