CA1068284A - Process for the preparation of hydantoin derivatives - Google Patents
Process for the preparation of hydantoin derivativesInfo
- Publication number
- CA1068284A CA1068284A CA260,695A CA260695A CA1068284A CA 1068284 A CA1068284 A CA 1068284A CA 260695 A CA260695 A CA 260695A CA 1068284 A CA1068284 A CA 1068284A
- Authority
- CA
- Canada
- Prior art keywords
- dichlorophenyl
- general formula
- acid
- hydantoin
- isopropylcarbamoyl
- 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.)
- Expired
Links
- 150000001469 hydantoins Chemical class 0.000 title claims abstract description 10
- 238000000034 method Methods 0.000 title claims description 14
- 238000002360 preparation method Methods 0.000 title claims description 4
- 229940053195 antiepileptics hydantoin derivative Drugs 0.000 title description 6
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims abstract description 21
- 239000002253 acid Substances 0.000 claims abstract description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 9
- UEDJUPKFFDUWHX-UHFFFAOYSA-N 2-[(3,5-dichlorophenyl)carbamoyl-(propan-2-ylcarbamoyl)amino]acetic acid Chemical compound CC(C)NC(=O)N(CC(O)=O)C(=O)NC1=CC(Cl)=CC(Cl)=C1 UEDJUPKFFDUWHX-UHFFFAOYSA-N 0.000 claims description 3
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 3
- 239000003495 polar organic solvent Substances 0.000 claims description 2
- 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 claims 3
- NSIPVRNFRCMFTE-UHFFFAOYSA-N 3-(3,5-dichlorophenyl)-2,4-dioxoimidazolidine-1-carboxamide Chemical compound O=C1N(C(=O)N)CC(=O)N1C1=CC(Cl)=CC(Cl)=C1 NSIPVRNFRCMFTE-UHFFFAOYSA-N 0.000 claims 1
- 150000007513 acids Chemical class 0.000 abstract description 3
- 239000000417 fungicide Substances 0.000 abstract 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- 238000003756 stirring Methods 0.000 description 11
- 239000000243 solution Substances 0.000 description 10
- 239000011541 reaction mixture Substances 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- 238000002844 melting Methods 0.000 description 7
- 230000008018 melting Effects 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- 239000000203 mixture Substances 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- WJRBRSLFGCUECM-UHFFFAOYSA-N hydantoin Chemical class O=C1CNC(=O)N1 WJRBRSLFGCUECM-UHFFFAOYSA-N 0.000 description 4
- 229940091173 hydantoin Drugs 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- AWUINPKCHSKCIS-UHFFFAOYSA-N 3-propan-2-ylimidazolidine-2,4-dione Chemical compound CC(C)N1C(=O)CNC1=O AWUINPKCHSKCIS-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- -1 acetic anhydride Chemical class 0.000 description 3
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 description 3
- 239000012948 isocyanate Substances 0.000 description 3
- 150000002513 isocyanates Chemical class 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
- 239000004471 Glycine Substances 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
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000012024 dehydrating agents Substances 0.000 description 2
- 125000004188 dichlorophenyl group Chemical group 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000001117 sulphuric acid Substances 0.000 description 2
- 235000011149 sulphuric acid Nutrition 0.000 description 2
- XEFUJGURFLOFAN-UHFFFAOYSA-N 1,3-dichloro-5-isocyanatobenzene Chemical compound ClC1=CC(Cl)=CC(N=C=O)=C1 XEFUJGURFLOFAN-UHFFFAOYSA-N 0.000 description 1
- URFDSEBDUGSCLZ-UHFFFAOYSA-N 1-(3,5-dichlorophenyl)imidazolidine-2,4-dione Chemical compound ClC1=CC(Cl)=CC(N2C(NC(=O)C2)=O)=C1 URFDSEBDUGSCLZ-UHFFFAOYSA-N 0.000 description 1
- JZQUNHVVWROPDZ-UHFFFAOYSA-N 2-(propan-2-ylcarbamoylamino)acetic acid Chemical compound CC(C)NC(=O)NCC(O)=O JZQUNHVVWROPDZ-UHFFFAOYSA-N 0.000 description 1
- GSLTVFIVJMCNBH-UHFFFAOYSA-N 2-isocyanatopropane Chemical compound CC(C)N=C=O GSLTVFIVJMCNBH-UHFFFAOYSA-N 0.000 description 1
- KZVRXPPUJQRGFN-UHFFFAOYSA-N N-carbamoylglycine Chemical compound NC(=O)NCC(O)=O KZVRXPPUJQRGFN-UHFFFAOYSA-N 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 239000011260 aqueous acid Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000002152 aqueous-organic solution Substances 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000003960 organic solvent Substances 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
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 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
-
- 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
- C07D233/74—Two oxygen atoms, e.g. hydantoin with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to other ring members
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 |
|---|---|---|---|
| FR7527883A FR2323688A1 (fr) | 1975-09-11 | 1975-09-11 | Nouveau procede de preparation de carbamoyl-1 (dichloro-3,5 phenyl)-3 hydantoines |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1068284A true CA1068284A (en) | 1979-12-18 |
Family
ID=9159861
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA260,695A Expired CA1068284A (en) | 1975-09-11 | 1976-09-08 | Process for the preparation of hydantoin derivatives |
Country Status (8)
| Country | Link |
|---|---|
| BR (1) | BR7605842A (enrdf_load_html_response) |
| CA (1) | CA1068284A (enrdf_load_html_response) |
| CH (1) | CH615921A5 (enrdf_load_html_response) |
| DD (1) | DD126533A5 (enrdf_load_html_response) |
| FR (1) | FR2323688A1 (enrdf_load_html_response) |
| GB (1) | GB1504840A (enrdf_load_html_response) |
| IE (1) | IE43549B1 (enrdf_load_html_response) |
| SU (1) | SU660593A3 (enrdf_load_html_response) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2483414A1 (fr) * | 1980-05-29 | 1981-12-04 | Rhone Poulenc Agrochimie | 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 |
| EP0041465B1 (fr) * | 1980-05-29 | 1984-07-25 | Rhone-Poulenc Agrochimie | Procédé de préparation de carbamoyl-1(dichloro-3,5-phényl)-3-hydantoines et chlorocarbonyl-1(dichloro-3,5-phényl)-3-hydantoine intermédiaire utilisable pour ce procédé |
| FR2494268A1 (fr) * | 1980-11-20 | 1982-05-21 | Rhone Poulenc Agrochimie | 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 |
| US5151524A (en) * | 1989-07-19 | 1992-09-29 | Otsuka Kagaku Kabushiki Kaisha | Process for preparing imidazolidine-2,5-dione derivative |
-
1975
- 1975-09-11 FR FR7527883A patent/FR2323688A1/fr active Granted
-
1976
- 1976-08-31 SU SU762392410A patent/SU660593A3/ru active
- 1976-09-03 BR BR7605842A patent/BR7605842A/pt unknown
- 1976-09-08 GB GB3722776A patent/GB1504840A/en not_active Expired
- 1976-09-08 CA CA260,695A patent/CA1068284A/en not_active Expired
- 1976-09-08 IE IE200776A patent/IE43549B1/en not_active IP Right Cessation
- 1976-09-10 CH CH1153676A patent/CH615921A5/fr not_active IP Right Cessation
- 1976-09-10 DD DD19473776A patent/DD126533A5/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| FR2323688A1 (fr) | 1977-04-08 |
| BR7605842A (pt) | 1977-08-16 |
| GB1504840A (en) | 1978-03-22 |
| IE43549B1 (en) | 1981-03-25 |
| SU660593A3 (ru) | 1979-04-30 |
| DD126533A5 (enrdf_load_html_response) | 1977-07-20 |
| IE43549L (en) | 1977-03-11 |
| CH615921A5 (en) | 1980-02-29 |
| FR2323688B1 (enrdf_load_html_response) | 1979-03-23 |
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