DEF0015129MA - - Google Patents
Info
- Publication number
- DEF0015129MA DEF0015129MA DEF0015129MA DE F0015129M A DEF0015129M A DE F0015129MA DE F0015129M A DEF0015129M A DE F0015129MA
- Authority
- DE
- Germany
- Prior art keywords
- anilide
- crotonic acid
- acid
- hydrogen
- anilides
- 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.)
- Active
Links
- 239000001257 hydrogen Substances 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 150000001875 compounds Chemical class 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 230000029936 alkylation Effects 0.000 claims description 3
- 238000005804 alkylation reaction Methods 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 2
- UHANVDZCDNSILX-UHFFFAOYSA-N n-phenylbutanamide Chemical class CCCC(=O)NC1=CC=CC=C1 UHANVDZCDNSILX-UHFFFAOYSA-N 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 19
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 238000002844 melting Methods 0.000 description 8
- 230000008018 melting Effects 0.000 description 8
- -1 ß-aminocrotonic acid anilides Chemical class 0.000 description 8
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 7
- 235000019441 ethanol Nutrition 0.000 description 7
- BZSYYMAHNJHZCB-QHHAFSJGSA-N (e)-n-phenylbut-2-enamide Chemical class C\C=C\C(=O)NC1=CC=CC=C1 BZSYYMAHNJHZCB-QHHAFSJGSA-N 0.000 description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 6
- 239000000155 melt Substances 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 229940051881 anilide analgesics and antipyretics Drugs 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 4
- DYRDKSSFIWVSNM-UHFFFAOYSA-N acetoacetanilide Chemical class CC(=O)CC(=O)NC1=CC=CC=C1 DYRDKSSFIWVSNM-UHFFFAOYSA-N 0.000 description 4
- 150000003931 anilides Chemical class 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 150000002431 hydrogen Chemical group 0.000 description 3
- 229940075930 picrate Drugs 0.000 description 3
- OXNIZHLAWKMVMX-UHFFFAOYSA-M picrate anion Chemical compound [O-]C1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-M 0.000 description 3
- OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical class OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- 230000001476 alcoholic effect Effects 0.000 description 2
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- 239000003589 local anesthetic agent Substances 0.000 description 2
- 229960005015 local anesthetics Drugs 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- YWTRXACYCWOQMR-FPLPWBNLSA-N (z)-3-amino-n-phenylbut-2-enamide Chemical compound C\C(N)=C\C(=O)NC1=CC=CC=C1 YWTRXACYCWOQMR-FPLPWBNLSA-N 0.000 description 1
- QFBAYOOKTYKPSI-UHFFFAOYSA-N 2-(butylamino)butanoic acid Chemical compound CCCCNC(CC)C(O)=O QFBAYOOKTYKPSI-UHFFFAOYSA-N 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229940124277 aminobutyric acid Drugs 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 1
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- WWROGCAUSKGAMX-UHFFFAOYSA-N n-(4-ethoxyphenyl)-3-oxobutanamide Chemical compound CCOC1=CC=C(NC(=O)CC(C)=O)C=C1 WWROGCAUSKGAMX-UHFFFAOYSA-N 0.000 description 1
- HKOURKRGAFKVFP-UHFFFAOYSA-N octacaine Chemical compound CCN(CC)C(C)CC(=O)NC1=CC=CC=C1 HKOURKRGAFKVFP-UHFFFAOYSA-N 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 230000002688 persistence Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 150000003139 primary aliphatic amines Chemical class 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 150000005619 secondary aliphatic amines Chemical class 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 230000007332 vesicle formation Effects 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 229940072358 xylocaine Drugs 0.000 description 1
Family
ID=
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE1620450C3 (de) | 1 - (2- Hydroxybenzyl) -2-piperazinomethylbenzimidazole, Verfahren zu ihrer Herstellung und diese enthaltende Arzneimittel | |
| DE967642C (de) | Verfahren zur Herstellung von basisch substituierten Buttersaeure-aniliden | |
| DEF0015129MA (enrdf_load_stackoverflow) | ||
| DE1111208B (de) | Verfahren zur Herstellung von hustenreizstillend wirkenden, basisch substituierten Diphenylcarbinolestern | |
| DE2329399A1 (de) | 4-alkyl-aminouracile, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel | |
| DE671787C (de) | Verfahren zur Darstellung von Pyrimidinverbindungen | |
| CH520117A (de) | Verfahren zur Herstellung von basisch substituierten Oximen des 5H-Dibenzo-(a,d)-10,11-dihydro-cyclohepten-5-ons | |
| DE1177633B (de) | Verfahren zur Herstellung aminoalkylierter 9,10-Dihydroanthracene | |
| DE949947C (de) | Verfahren zur Herstellung von basischen Bis-N-phenylurethanen | |
| DE614596C (de) | Verfahren zur Darstellung von ?-Glyoxalidinarylmethylolen | |
| DE1018869B (de) | Verfahren zur Herstellung von Aminoalkylpurinderivaten | |
| DE2245248C2 (de) | 1-Phenyl-4-aminopyridaziniumsalze | |
| DE159692C (enrdf_load_stackoverflow) | ||
| DE208255C (enrdf_load_stackoverflow) | ||
| AT319960B (de) | Verfahren zur Herstellung von neuen Pyridazinverbindungen | |
| DE1493522C (de) | Verfahren zur Herstellung von Diphenyl propylaminderivaten | |
| AT360522B (de) | Verfahren zur herstellung von neuen thiazoli- dinderivaten und ihren salzen | |
| AT267527B (de) | Verfahren zur Herstellung neuer substituierter Aminopyridine, von deren Salzen und optisch aktiven Isomeren | |
| CH336815A (de) | Verfahren zur Herstellung von basisch substituierten Buttersäureaniliden | |
| AT210882B (de) | Verfahren zur Herstellung von neuen substituierten Aminoacetophenonen und deren Salzen | |
| DE916170C (de) | Verfahren zur Herstellung von 1-(3', 4'-Dioxyphenyl)-2-aralkylamino-aethanolen | |
| DE1470260C (de) | 3,5 Dioxopyrazoiidinderivate und ein Verfahren zu ihrer Herstellung | |
| DD228812A1 (de) | Neues verfahren zur herstellung n-substituierter hexahydro-pyridazin- und diazanorbornan-2,3-dicarboximide | |
| DE623373C (enrdf_load_stackoverflow) | ||
| DE1184344B (de) | Verfahren zur Herstellung von Isochinolinderivaten |