CH615921A5 - Process for the preparation of 1-carbamoyl-3-(3,5-dichlorophenyl)hydantoins - Google Patents
Process for the preparation of 1-carbamoyl-3-(3,5-dichlorophenyl)hydantoins Download PDFInfo
- Publication number
- CH615921A5 CH615921A5 CH1153676A CH1153676A CH615921A5 CH 615921 A5 CH615921 A5 CH 615921A5 CH 1153676 A CH1153676 A CH 1153676A CH 1153676 A CH1153676 A CH 1153676A CH 615921 A5 CH615921 A5 CH 615921A5
- Authority
- CH
- Switzerland
- Prior art keywords
- general formula
- dichloro
- phenyl
- carbamoyl
- hydantoin
- Prior art date
Links
- 150000001469 hydantoins Chemical class 0.000 title claims abstract description 6
- 238000000034 method Methods 0.000 title claims description 8
- 238000002360 preparation method Methods 0.000 title claims description 3
- 239000002253 acid Substances 0.000 claims abstract description 6
- -1 3,5-dichloro-phenyl Chemical group 0.000 claims description 20
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical group CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 18
- 238000007363 ring formation reaction Methods 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 239000003495 polar organic solvent Substances 0.000 claims description 3
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical group CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 150000007524 organic acids Chemical class 0.000 claims description 2
- 150000008064 anhydrides Chemical class 0.000 claims 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 239000000417 fungicide Substances 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- WJRBRSLFGCUECM-UHFFFAOYSA-N hydantoin Chemical compound O=C1CNC(=O)N1 WJRBRSLFGCUECM-UHFFFAOYSA-N 0.000 description 11
- 229940091173 hydantoin Drugs 0.000 description 11
- 238000003756 stirring Methods 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
- 238000001914 filtration Methods 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-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
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 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
- 239000000203 mixture Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- XEFUJGURFLOFAN-UHFFFAOYSA-N 1,3-dichloro-5-isocyanatobenzene Chemical compound ClC1=CC(Cl)=CC(N=C=O)=C1 XEFUJGURFLOFAN-UHFFFAOYSA-N 0.000 description 2
- AWUINPKCHSKCIS-UHFFFAOYSA-N 3-propan-2-ylimidazolidine-2,4-dione Chemical compound CC(C)N1C(=O)CNC1=O AWUINPKCHSKCIS-UHFFFAOYSA-N 0.000 description 2
- 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
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000012024 dehydrating agents Substances 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- GSLTVFIVJMCNBH-UHFFFAOYSA-N 2-isocyanatopropane Chemical compound CC(C)N=C=O GSLTVFIVJMCNBH-UHFFFAOYSA-N 0.000 description 1
- 239000004471 Glycine Substances 0.000 description 1
- KZVRXPPUJQRGFN-UHFFFAOYSA-N N-carbamoylglycine Chemical compound NC(=O)NCC(O)=O KZVRXPPUJQRGFN-UHFFFAOYSA-N 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
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000011260 aqueous acid Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- 238000004061 bleaching Methods 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 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
- 230000000855 fungicidal effect Effects 0.000 description 1
- 239000003292 glue Substances 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 239000011707 mineral Substances 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
- 239000012429 reaction media Substances 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 |
|---|---|
| CH615921A5 true CH615921A5 (en) | 1980-02-29 |
Family
ID=9159861
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1153676A CH615921A5 (en) | 1975-09-11 | 1976-09-10 | Process for the preparation of 1-carbamoyl-3-(3,5-dichlorophenyl)hydantoins |
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 |
| CA1068284A (en) | 1979-12-18 |
| 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 |
| FR2323688B1 (enrdf_load_html_response) | 1979-03-23 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |