PL61568B1 - - Google Patents
Download PDFInfo
- Publication number
- PL61568B1 PL61568B1 PL116988A PL11698866A PL61568B1 PL 61568 B1 PL61568 B1 PL 61568B1 PL 116988 A PL116988 A PL 116988A PL 11698866 A PL11698866 A PL 11698866A PL 61568 B1 PL61568 B1 PL 61568B1
- Authority
- PL
- Poland
- Prior art keywords
- group
- general formula
- lower alkyl
- compound
- groups
- Prior art date
Links
- 239000011541 reaction mixture Substances 0.000 claims description 11
- -1 hydrogen sulfide ions Chemical class 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 4
- 229910000037 hydrogen sulfide Inorganic materials 0.000 claims description 2
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims 5
- 150000001875 compounds Chemical class 0.000 claims 4
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- 125000004076 pyridyl group Chemical group 0.000 claims 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
- 101000913968 Ipomoea purpurea Chalcone synthase C Proteins 0.000 claims 1
- 101000907988 Petunia hybrida Chalcone-flavanone isomerase C Proteins 0.000 claims 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 1
- 125000003710 aryl alkyl group Chemical group 0.000 claims 1
- 239000003153 chemical reaction reagent Substances 0.000 claims 1
- 125000000524 functional group Chemical group 0.000 claims 1
- 238000010438 heat treatment Methods 0.000 claims 1
- 230000007062 hydrolysis Effects 0.000 claims 1
- 238000006460 hydrolysis reaction Methods 0.000 claims 1
- 150000002460 imidazoles Chemical class 0.000 claims 1
- 238000011065 in-situ storage Methods 0.000 claims 1
- 229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 claims 1
- 230000003647 oxidation Effects 0.000 claims 1
- 238000007254 oxidation reaction Methods 0.000 claims 1
- 239000002798 polar solvent Substances 0.000 claims 1
- 125000002924 primary amino group Chemical class [H]N([H])* 0.000 claims 1
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 25
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 20
- 239000000243 solution Substances 0.000 description 18
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- LGDSHSYDSCRFAB-UHFFFAOYSA-N Methyl isothiocyanate Chemical compound CN=C=S LGDSHSYDSCRFAB-UHFFFAOYSA-N 0.000 description 14
- 239000000203 mixture Substances 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- 238000001953 recrystallisation Methods 0.000 description 7
- 238000010992 reflux Methods 0.000 description 7
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical class [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 238000000354 decomposition reaction Methods 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 229910052938 sodium sulfate Inorganic materials 0.000 description 4
- 235000011152 sodium sulphate Nutrition 0.000 description 4
- RGYNOPLNIDBIGT-UHFFFAOYSA-N 4-(4-chlorophenyl)-3-methyl-1h-imidazole-2-thione Chemical compound N1C(=S)N(C)C(C=2C=CC(Cl)=CC=2)=C1 RGYNOPLNIDBIGT-UHFFFAOYSA-N 0.000 description 3
- 239000002026 chloroform extract Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- ISJSMIGFALWQBH-UHFFFAOYSA-N 4-(4-methoxyphenyl)-3-methyl-1h-imidazole-2-thione Chemical compound C1=CC(OC)=CC=C1C1=CNC(=S)N1C ISJSMIGFALWQBH-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- PLVQZWFZVFASKS-UHFFFAOYSA-N CN1C(=NC(=C1C1=CC=C(C=C1)OC)C)S Chemical compound CN1C(=NC(=C1C1=CC=C(C=C1)OC)C)S PLVQZWFZVFASKS-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- FHOSFKLVCXFTBV-UHFFFAOYSA-N 1-(4-fluorophenyl)-3-(2-hydroxyethyl)thiourea Chemical compound OCCNC(=S)NC1=CC=C(F)C=C1 FHOSFKLVCXFTBV-UHFFFAOYSA-N 0.000 description 1
- NFIUJHJMCQQYDL-UHFFFAOYSA-N 1-fluoro-4-isothiocyanatobenzene Chemical compound FC1=CC=C(N=C=S)C=C1 NFIUJHJMCQQYDL-UHFFFAOYSA-N 0.000 description 1
- GWYZXHXGBADGGC-UHFFFAOYSA-N 3-(4-fluorophenyl)-1h-imidazole-2-thione Chemical compound C1=CC(F)=CC=C1N1C(S)=NC=C1 GWYZXHXGBADGGC-UHFFFAOYSA-N 0.000 description 1
- FXPJQESWXQDJOW-UHFFFAOYSA-N 4-(4-chlorophenyl)-1,3-dihydroimidazole-2-thione Chemical compound C1=CC(Cl)=CC=C1C1=CNC(=S)N1 FXPJQESWXQDJOW-UHFFFAOYSA-N 0.000 description 1
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 1
- ZOQMXJXYIZXROV-UHFFFAOYSA-N CN1C(=NC(=C1C1=CC=C(C=C1)C)C)S Chemical compound CN1C(=NC(=C1C1=CC=C(C=C1)C)C)S ZOQMXJXYIZXROV-UHFFFAOYSA-N 0.000 description 1
- OBKDSNYXRLJJNL-UHFFFAOYSA-N CN1C(=NC(=C1C1=CC=C(C=C1)F)C)S Chemical compound CN1C(=NC(=C1C1=CC=C(C=C1)F)C)S OBKDSNYXRLJJNL-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- OWAQXCQNWNJICI-UHFFFAOYSA-N benzene;chloroform Chemical compound ClC(Cl)Cl.C1=CC=CC=C1 OWAQXCQNWNJICI-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- IQFVPQOLBLOTPF-HKXUKFGYSA-L congo red Chemical compound [Na+].[Na+].C1=CC=CC2=C(N)C(/N=N/C3=CC=C(C=C3)C3=CC=C(C=C3)/N=N/C3=C(C4=CC=CC=C4C(=C3)S([O-])(=O)=O)N)=CC(S([O-])(=O)=O)=C21 IQFVPQOLBLOTPF-HKXUKFGYSA-L 0.000 description 1
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- MYWQGROTKMBNKN-UHFFFAOYSA-N tributoxyalumane Chemical compound [Al+3].CCCC[O-].CCCC[O-].CCCC[O-] MYWQGROTKMBNKN-UHFFFAOYSA-N 0.000 description 1
- 238000002211 ultraviolet spectrum Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PL61568B1 true PL61568B1 (enFirst) | 1970-10-25 |
Family
ID=
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| USRE29668E (en) | Glycineamides | |
| DE1695093A1 (de) | Neue Imidazolderivate | |
| SU450398A3 (ru) | Способ получени -арил-2аминоалкоксистиролов | |
| US20090082578A1 (en) | Process for the synthesis of strontium ranelate and its hydrates | |
| PL111873B1 (en) | Process for preparing novel 3-phenyl-5-substituted-/1h/-pyridinothiones-4 | |
| NO122789B (enFirst) | ||
| DE69527787T2 (de) | Verfahren und zwischenprodukte zur herstellung von piperazinderivaten | |
| JPS6126538B2 (enFirst) | ||
| GB2117774A (en) | Oximinoacetic acid derivatives | |
| US2871243A (en) | 5-amino-3-methyl-isothiazole and process | |
| EP0107622B1 (de) | Neue Benzodioxolderivate, Verfahren zu deren Herstellung und entsprechende pharmazeutische Zusammensetzungen | |
| PL61568B1 (enFirst) | ||
| DE2436263A1 (de) | Thiazolidinderivate und verfahren zu ihrer herstellung | |
| DE2624254C2 (de) | Verfahren zur Herstellung von Thieno[3,2-c]pyridinen | |
| US3264316A (en) | Certain 2-acylimino-3-substitutedthiazoline-4 compounds | |
| PL88905B1 (enFirst) | ||
| PL84712B1 (enFirst) | ||
| US2827457A (en) | department of commerce | |
| US2377395A (en) | Pyrimidine derivatives and peocesb | |
| US2535971A (en) | 1-carbalkoxy-4-substituted piperazines | |
| US3135759A (en) | Manotactuse of organic chemical | |
| DE2758613C2 (de) | Sulfoximide, Verfahren zu ihrer Herstellung und diese enthaltende Arzneimittel | |
| SU492090A3 (ru) | Способ получени производных имидазо (2,1- )тиазола | |
| AT273154B (de) | Verfahren zur Herstellung von neuen Sulfonylharnstoffderivaten | |
| SU920056A1 (ru) | Способ получени R,S-2,3,5,6-тетрагидро-6-фенилимидазо /2.1-в/-тиазола |