SU1318157A3 - Способ получени производных 1-карбамоил-3-(3,5-дихлорфенил)-гидантоина - Google Patents
Способ получени производных 1-карбамоил-3-(3,5-дихлорфенил)-гидантоина Download PDFInfo
- Publication number
- SU1318157A3 SU1318157A3 SU813285400A SU3285400A SU1318157A3 SU 1318157 A3 SU1318157 A3 SU 1318157A3 SU 813285400 A SU813285400 A SU 813285400A SU 3285400 A SU3285400 A SU 3285400A SU 1318157 A3 SU1318157 A3 SU 1318157A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- hydantoin
- mol
- phenyl
- carbamoyl
- dichlorophenyl
- Prior art date
Links
- 229940091173 hydantoin Drugs 0.000 title claims description 12
- 238000004519 manufacturing process Methods 0.000 title 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims abstract description 7
- 239000002253 acid Substances 0.000 claims abstract description 4
- 238000006243 chemical reaction Methods 0.000 claims abstract description 4
- 239000003960 organic solvent Substances 0.000 claims abstract 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 7
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 6
- -1 3,5-dichlorophenyl Chemical group 0.000 claims description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 3
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 125000000467 secondary amino group Chemical class [H]N([*:1])[*:2] 0.000 claims 1
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 abstract description 23
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 abstract description 5
- OGCORJSEYZKHIN-UHFFFAOYSA-N 3-(3,5-dichlorophenyl)imidazolidine-2,4-dione Chemical compound ClC1=CC(Cl)=CC(N2C(NCC2=O)=O)=C1 OGCORJSEYZKHIN-UHFFFAOYSA-N 0.000 abstract 1
- ONUFESLQCSAYKA-UHFFFAOYSA-N iprodione Chemical compound O=C1N(C(=O)NC(C)C)CC(=O)N1C1=CC(Cl)=CC(Cl)=C1 ONUFESLQCSAYKA-UHFFFAOYSA-N 0.000 abstract 1
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 4
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 238000009833 condensation Methods 0.000 description 4
- 230000005494 condensation Effects 0.000 description 4
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 3
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 229960000549 4-dimethylaminophenol Drugs 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000002826 coolant Substances 0.000 description 2
- SHFJWMWCIHQNCP-UHFFFAOYSA-M hydron;tetrabutylazanium;sulfate Chemical compound OS([O-])(=O)=O.CCCC[N+](CCCC)(CCCC)CCCC SHFJWMWCIHQNCP-UHFFFAOYSA-M 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- ZJTJUVIJVLLGSP-UHFFFAOYSA-N Lumichrome Natural products N1C(=O)NC(=O)C2=C1N=C1C=C(C)C(C)=CC1=N2 ZJTJUVIJVLLGSP-UHFFFAOYSA-N 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 241001122767 Theaceae Species 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 229940053195 antiepileptics hydantoin derivative Drugs 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 238000007872 degassing Methods 0.000 description 1
- 125000003963 dichloro group Chemical group Cl* 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- WJRBRSLFGCUECM-UHFFFAOYSA-N hydantoin Chemical compound O=C1CNC(=O)N1 WJRBRSLFGCUECM-UHFFFAOYSA-N 0.000 description 1
- 150000001469 hydantoins Chemical class 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two 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
- C07D233/72—Two oxygen atoms, e.g. hydantoin
- C07D233/80—Two oxygen atoms, e.g. hydantoin with hetero atoms or acyl radicals directly attached to ring nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8012238A FR2483414A1 (fr) | 1980-05-29 | 1980-05-29 | Procede de preparation de carbamoyl-1(dichloro-3,5-phenyl)-3-hydantoines et chlorocarbonyl-1(dichloro-3,5-phenyl)-3-hydantoine intermediaire utilisable pour ce procede |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU1318157A3 true SU1318157A3 (ru) | 1987-06-15 |
Family
ID=9242608
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU813285400A SU1318157A3 (ru) | 1980-05-29 | 1981-05-26 | Способ получени производных 1-карбамоил-3-(3,5-дихлорфенил)-гидантоина |
Country Status (5)
| Country | Link |
|---|---|
| KR (1) | KR840001563B1 (enExample) |
| FR (1) | FR2483414A1 (enExample) |
| HU (1) | HU193851B (enExample) |
| SU (1) | SU1318157A3 (enExample) |
| ZA (1) | ZA813601B (enExample) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2174119C2 (ru) * | 1996-06-05 | 2001-09-27 | Хехст Акциенгезельшафт | Соли этилового эфира 3-(2-(4-(4-(аминоиминометил)фенил)-4-метил-2,5-диоксоимидазолидин-1-ил)ацетиламино)-3-фенилпропионовой кислоты, способ их получения и фармацевтическая композиция на их основе |
| RU2213737C2 (ru) * | 1997-09-18 | 2003-10-10 | Авентис Фарма Дойчланд Гмбх | Новые производные имидазолидина, их получение, их применение и содержащие их фармацевтические препараты |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2120222A5 (en) * | 1970-10-06 | 1972-08-18 | Rhone Poulenc Sa | N-acyl-hydantoin derivs - with fungicidal activity |
| FR2323688A1 (fr) * | 1975-09-11 | 1977-04-08 | Rhone Poulenc Ind | Nouveau procede de preparation de carbamoyl-1 (dichloro-3,5 phenyl)-3 hydantoines |
| DE2550964A1 (de) * | 1975-11-13 | 1977-08-04 | Basf Ag | Hydantoinderivate |
-
1980
- 1980-05-29 FR FR8012238A patent/FR2483414A1/fr active Granted
-
1981
- 1981-05-23 KR KR1019810001823A patent/KR840001563B1/ko not_active Expired
- 1981-05-26 SU SU813285400A patent/SU1318157A3/ru active
- 1981-05-27 ZA ZA00813601A patent/ZA813601B/xx unknown
- 1981-05-28 HU HU861004A patent/HU193851B/hu not_active IP Right Cessation
Non-Patent Citations (1)
| Title |
|---|
| Патент FR № 2148868, кл. С 07 D 49/00, опублик. 1973. * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2174119C2 (ru) * | 1996-06-05 | 2001-09-27 | Хехст Акциенгезельшафт | Соли этилового эфира 3-(2-(4-(4-(аминоиминометил)фенил)-4-метил-2,5-диоксоимидазолидин-1-ил)ацетиламино)-3-фенилпропионовой кислоты, способ их получения и фармацевтическая композиция на их основе |
| RU2213737C2 (ru) * | 1997-09-18 | 2003-10-10 | Авентис Фарма Дойчланд Гмбх | Новые производные имидазолидина, их получение, их применение и содержащие их фармацевтические препараты |
Also Published As
| Publication number | Publication date |
|---|---|
| KR840001563B1 (ko) | 1984-10-05 |
| FR2483414A1 (fr) | 1981-12-04 |
| KR830006227A (ko) | 1983-09-20 |
| ZA813601B (en) | 1982-06-30 |
| HU193851B (en) | 1987-12-28 |
| FR2483414B1 (enExample) | 1982-11-12 |
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