SU271413A1 - - Google Patents
Info
- Publication number
- SU271413A1 SU271413A1 SU1298927A SU1298927A SU271413A1 SU 271413 A1 SU271413 A1 SU 271413A1 SU 1298927 A SU1298927 A SU 1298927A SU 1298927 A SU1298927 A SU 1298927A SU 271413 A1 SU271413 A1 SU 271413A1
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- hydantoin
- solution
- ethanol
- ether
- nitrofurfurylideneamino
- Prior art date
Links
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- 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 claims description 5
- 238000009835 boiling Methods 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- NXLNNXIXOYSCMB-UHFFFAOYSA-N (4-nitrophenyl) carbonochloridate Chemical compound [O-][N+](=O)C1=CC=C(OC(Cl)=O)C=C1 NXLNNXIXOYSCMB-UHFFFAOYSA-N 0.000 claims description 3
- SXINBFXPADXIEY-UHFFFAOYSA-N 5-Nitrofurfural Chemical compound [O-][N+](=O)C1=CC=C(C=O)O1 SXINBFXPADXIEY-UHFFFAOYSA-N 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims 2
- 125000004429 atom Chemical group 0.000 claims 1
- 230000003993 interaction Effects 0.000 claims 1
- 238000002955 isolation Methods 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 24
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 21
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 16
- 239000000243 solution Substances 0.000 description 16
- -1 nitrofurfurylidene Chemical class 0.000 description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- 238000002844 melting Methods 0.000 description 8
- 230000008018 melting Effects 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 229940091173 hydantoin Drugs 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- WJRBRSLFGCUECM-UHFFFAOYSA-N hydantoin Chemical compound O=C1CNC(=O)N1 WJRBRSLFGCUECM-UHFFFAOYSA-N 0.000 description 3
- 239000000155 melt Substances 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- FHLXUWOHGKLDNF-UHFFFAOYSA-N (2-nitrophenyl) carbonochloridate Chemical compound [O-][N+](=O)C1=CC=CC=C1OC(Cl)=O FHLXUWOHGKLDNF-UHFFFAOYSA-N 0.000 description 2
- MJWVOJJALJAWBK-UHFFFAOYSA-N 3-[(5-nitrofuran-2-yl)methylideneamino]imidazolidine-2,4-dione Chemical compound O1C([N+](=O)[O-])=CC=C1C=NN1C(=O)NCC1=O MJWVOJJALJAWBK-UHFFFAOYSA-N 0.000 description 2
- DCROTKUJYXYESN-UHFFFAOYSA-N 3-aminoimidazolidine-2,4-dione Chemical compound NN1C(=O)CNC1=O DCROTKUJYXYESN-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 150000001469 hydantoins Chemical class 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 229940071089 sarcosinate Drugs 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- HLKXHLYVDRXXIA-UHFFFAOYSA-N (5-nitrofuran-2-yl)methanimine Chemical compound [O-][N+](=O)C1=CC=C(C=N)O1 HLKXHLYVDRXXIA-UHFFFAOYSA-N 0.000 description 1
- OVZGKCAMDOQKMB-UHFFFAOYSA-N 3-amino-1-methylimidazolidine-2,4-dione Chemical compound CN1CC(=O)N(N)C1=O OVZGKCAMDOQKMB-UHFFFAOYSA-N 0.000 description 1
- DHMQDGOQFOQNFH-UHFFFAOYSA-M Aminoacetate Chemical compound NCC([O-])=O DHMQDGOQFOQNFH-UHFFFAOYSA-M 0.000 description 1
- MFFMCTWELGRJAH-UHFFFAOYSA-N C(C)(C)N1C(=O)N(C(=O)C1)N Chemical compound C(C)(C)N1C(=O)N(C(=O)C1)N MFFMCTWELGRJAH-UHFFFAOYSA-N 0.000 description 1
- 241000289669 Erinaceus europaeus Species 0.000 description 1
- HXEACLLIILLPRG-YFKPBYRVSA-N L-pipecolic acid Chemical compound [O-]C(=O)[C@@H]1CCCC[NH2+]1 HXEACLLIILLPRG-YFKPBYRVSA-N 0.000 description 1
- RZGYTMFRBLCVDF-UHFFFAOYSA-N [N+](=O)([O-])C1=CC=C(C=C1)OC(=O)N(CC(=O)OCC)C(C)C Chemical compound [N+](=O)([O-])C1=CC=C(C=C1)OC(=O)N(CC(=O)OCC)C(C)C RZGYTMFRBLCVDF-UHFFFAOYSA-N 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 229940053195 antiepileptics hydantoin derivative Drugs 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- BTKSUULMJNNXHG-UHFFFAOYSA-N ethyl 2-(methylamino)acetate Chemical compound CCOC(=O)CNC BTKSUULMJNNXHG-UHFFFAOYSA-N 0.000 description 1
- FSYKKLYZXJSNPZ-UHFFFAOYSA-N sarcosine Chemical compound C[NH2+]CC([O-])=O FSYKKLYZXJSNPZ-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU271413A1 true SU271413A1 (cs) |
Family
ID=
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| FR2643903A1 (fr) | Nouveaux derives de benzimidazole, leurs procedes de preparation, intermediaires de synthese, compositions pharmaceutiques les contenant, utiles notamment pour le traitement des maladies cardiovasculaires, et des ulceres duodenaux | |
| CZ260494A3 (en) | Indole derivatives, process of their preparation, intermediates for their preparation and medicaments based thereon | |
| JPH089610B2 (ja) | 置換イソフラボン誘導体の改良された製造方法 | |
| US4612318A (en) | CNS-depressant and analgesic tricyclo-[pyrazolo-[3,4-6]-pyridine] derivatives and pharmaceutical compositions thereof | |
| US4308384A (en) | Production of triazinones | |
| SU271413A1 (cs) | ||
| WO2008034644A2 (en) | Process for making anastrozole | |
| US3847934A (en) | 7-(imidazolinyl-(2)-amino)-indazoles | |
| WO1998005657A1 (en) | 2,3-dihydro-1,4-benzothiazepines, their preparation and their use as intermediates | |
| US3487083A (en) | Preparation of 4-hydroxypyrazolo(3,4-d)pyrimidine | |
| EP0000301B1 (fr) | Procédé de préparation de thiéno(2,3-c) et thiéno(3,2-c) pyridines | |
| FR2510109A1 (fr) | Acide 7-alcoxycarbonyl-6,8-dimethyl-1-phtalazone-4-a-hydroxyacetique et son procede de preparation | |
| JPH05271200A (ja) | ６，７−ジクロロ−１，５−ジヒドロ−イミダゾ〔２，１−ｂ〕キナゾリン−２〔３Ｈ〕−オンの製造方法 | |
| Bogert et al. | THE DIRECT SYNTHESIS OF KETODIHYDROQUINAZOLINS FROM ORTHOAMINO ACIDS. | |
| US4146713A (en) | Method of preparing 3-morpholino-2-cyanoacrylamide | |
| AU2004230326B2 (en) | Method for synthesising 5-chloro-1-aryl-4-(4, 5-dicyano-1H-imidazol-2-yl)-3-alkyl-1H-pyrazole derivatives | |
| SU268303A1 (ru) | Способ получения производных гидразинопиридазинов | |
| FR2485534A1 (fr) | 6-hydrazono-pyrido(2,1-b)quinazoline-11-ones et procede pour leur preparation | |
| EP0145236A2 (en) | Thiadiazinone compounds, process for their preparation, and pharmaceutical compositions containing them | |
| NZ257551A (en) | Preparation of 6-[(4-chlorophenyl)(1h-1,2,4-triazol-1-yl)methyl]-1-methyl-1h-benzotriazole in enantiomerically pure form;intermediates | |
| US4980495A (en) | Trialkylamine salts of 3-chloro-1,1-dicyano-2-hydroxy-1-propene and preparation of 2-amino-4-chloro-3-cyano-5-formylthiophene | |
| SU231412A1 (ru) | Способ получения замещенных 1,2-днгидро-1,2,4- | |
| KR0156327B1 (ko) | 벤즈 또는 피리도이미다졸 유도체 | |
| US3736316A (en) | 1,2,5-benzotriazepin-4-ones and their preparation | |
| WO2023006986A1 (en) | Method for preparing and purifying an agent suitable for treating anemia |