DE1254634B - Verfahren zur Herstellung von 1-Aryl-hydropyrazolen - Google Patents
Verfahren zur Herstellung von 1-Aryl-hydropyrazolenInfo
- Publication number
- DE1254634B DE1254634B DEG37697A DEG0037697A DE1254634B DE 1254634 B DE1254634 B DE 1254634B DE G37697 A DEG37697 A DE G37697A DE G0037697 A DEG0037697 A DE G0037697A DE 1254634 B DE1254634 B DE 1254634B
- Authority
- DE
- Germany
- Prior art keywords
- aryl
- phenyl
- hydropyrazoles
- formula
- preparation
- 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 15
- 238000002360 preparation method Methods 0.000 title claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 150000004985 diamines Chemical class 0.000 claims description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 6
- 239000000243 solution Substances 0.000 description 5
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000005708 Sodium hypochlorite Substances 0.000 description 3
- 150000004982 aromatic amines Chemical class 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- -1 methoxy, ethoxy, cyclohexyloxy, benzyloxy Chemical group 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- MHQSQCVXHDWARZ-UHFFFAOYSA-N 1-phenylpyrazolidine Chemical compound C1CCNN1C1=CC=CC=C1 MHQSQCVXHDWARZ-UHFFFAOYSA-N 0.000 description 2
- JFJWVJAVVIQZRT-UHFFFAOYSA-N 2-phenyl-1,3-dihydropyrazole Chemical compound C1C=CNN1C1=CC=CC=C1 JFJWVJAVVIQZRT-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 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 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- QWPPOHNGKGFGJK-UHFFFAOYSA-N hypochlorous acid Chemical compound ClO QWPPOHNGKGFGJK-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- DOSWHECVUKBMCG-UHFFFAOYSA-N n'-phenylpropane-1,3-diamine Chemical compound NCCCNC1=CC=CC=C1 DOSWHECVUKBMCG-UHFFFAOYSA-N 0.000 description 2
- 150000002825 nitriles Chemical class 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- OZYNUJIWEYOJOK-UHFFFAOYSA-N N1NCC=C1.N1NCCC1 Chemical compound N1NCC=C1.N1NCCC1 OZYNUJIWEYOJOK-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 125000004062 acenaphthenyl group Chemical class C1(CC2=CC=CC3=CC=CC1=C23)* 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 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
- 159000000007 calcium salts Chemical class 0.000 description 1
- 125000000000 cycloalkoxy group Chemical group 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- RXKJFZQQPQGTFL-UHFFFAOYSA-N dihydroxyacetone Chemical compound OCC(=O)CO RXKJFZQQPQGTFL-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- CUILPNURFADTPE-UHFFFAOYSA-N hypobromous acid Chemical compound BrO CUILPNURFADTPE-UHFFFAOYSA-N 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- CFZNHLDJLPGVSQ-UHFFFAOYSA-N pentyl hypobromite Chemical compound CCCCCOBr CFZNHLDJLPGVSQ-UHFFFAOYSA-N 0.000 description 1
- USHDBZLNUZHGOP-UHFFFAOYSA-N pentyl hypochlorite Chemical compound CCCCCOCl USHDBZLNUZHGOP-UHFFFAOYSA-N 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- DNXIASIHZYFFRO-UHFFFAOYSA-N pyrazoline Chemical compound C1CN=NC1 DNXIASIHZYFFRO-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- CRWJEUDFKNYSBX-UHFFFAOYSA-N sodium;hypobromite Chemical compound [Na+].Br[O-] CRWJEUDFKNYSBX-UHFFFAOYSA-N 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 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
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 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
- C07D231/04—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K15/00—Anti-oxidant compositions; Compositions inhibiting chemical change
- C09K15/04—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds
- C09K15/30—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds containing heterocyclic ring with at least one nitrogen atom as ring member
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH555062A CH409978A (de) | 1962-05-09 | 1962-05-09 | Verfahren zur Herstellung von 1-Aryl-hydropyrazolen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1254634B true DE1254634B (de) | 1967-11-23 |
Family
ID=4295451
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEG37697A Pending DE1254634B (de) | 1962-05-09 | 1963-05-08 | Verfahren zur Herstellung von 1-Aryl-hydropyrazolen |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US3236858A (en, 2012) |
| BE (1) | BE632034A (en, 2012) |
| CH (1) | CH409978A (en, 2012) |
| DE (1) | DE1254634B (en, 2012) |
| GB (1) | GB982710A (en, 2012) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4547518A (en) * | 1984-04-06 | 1985-10-15 | A. H. Robins Company, Incorporated | Antiemetic N-(1-substituted-4,5-dihydro-1H-pyrazol-4-yl)benzamides |
-
0
- BE BE632034D patent/BE632034A/xx unknown
-
1962
- 1962-05-09 CH CH555062A patent/CH409978A/de unknown
-
1963
- 1963-04-26 US US276075A patent/US3236858A/en not_active Expired - Lifetime
- 1963-05-08 DE DEG37697A patent/DE1254634B/de active Pending
- 1963-05-08 GB GB18139/63A patent/GB982710A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| BE632034A (en, 2012) | |
| CH409978A (de) | 1966-03-31 |
| US3236858A (en) | 1966-02-22 |
| GB982710A (en) | 1965-02-10 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE1216882B (de) | Verfahren zur Herstellung von neuen substituierten Diphenylaethern | |
| DE3235933A1 (de) | Verfahren zur herstellung bicyclischer orthoesteramide | |
| DE1670522A1 (de) | Verfahren zur Herstellung neuer substituierter Aminopyridine | |
| DE1159462B (de) | Verfahren zur Herstellung von s-Triazinderivaten | |
| DE1254634B (de) | Verfahren zur Herstellung von 1-Aryl-hydropyrazolen | |
| DE1965872A1 (de) | Ungesaettigte Verbindungen mit einer Aminomethylengruppe,Verfahren zu ihrer Herstellung und ihre Verwendung | |
| DE1543429A1 (de) | Verfahren zur Herstellung von Dimeren und Trimeren von Acrylaten | |
| CH500982A (de) | Verfahren zur Herstellung von 3-Phenyl-7-amino-carbostyril-Verbindungen | |
| DE1568622A1 (de) | Verfahren zur Herstellung neuartiger Phenolderivate | |
| DE1206879B (de) | Verfahren zur Herstellung von p-Aminoarylaldehyden | |
| DE2655794C2 (de) | Verfahren zur Herstellung von Äthylencyanhydrin | |
| DE1129947B (de) | Verfahren zur Herstellung von 1, 4-Bis-(p-carboxystyryl)-benzolen | |
| DE1096905B (de) | Verfahren zur Herstellung von organischen Phosphinen | |
| DE1216302B (de) | Verfahren zur Herstellung von Polyorganocyclosiloxanen | |
| AT222104B (de) | Verfahren zur Herstellung von neuen Cyclobutanderivaten | |
| EP0101996B1 (de) | Verfahren zur Herstellung von E-Isomeren von 1-Cyclohexyl-2-(1,2,4-triazol-1-yl)-1-penten-3-on-Derivaten | |
| DE1271713B (de) | Verfahren zur Herstellung von organischen Carbonylverbindungen | |
| DE955770C (de) | Verfahren zur Herstellung von basisch substituierten Carbonsaeureamiden | |
| DE1174787B (de) | Verfahren zur Herstellung von 4, 4'-Methenyl-bis-[pyrazolonen-(5)] | |
| DE1163803B (de) | Verfahren zur Herstellung von 3-Aryl-1,1,3,3-tetrachlor-2-aza-propenen | |
| DE2302844A1 (de) | 2-thiazolon-5-carbonsaeure-derivate | |
| DE2609864A1 (de) | Verfahren zur herstellung von 3-amino-1,2-benzisothiazolen | |
| DE1272286C2 (de) | Verfahren zur Herstellung von N-substituierten aliphatischen Thiocarbonsaeureamiden | |
| AT223204B (de) | Verfahren zur Herstellung von neuen Azepinderivaten | |
| AT267527B (de) | Verfahren zur Herstellung neuer substituierter Aminopyridine, von deren Salzen und optisch aktiven Isomeren |