FR2504132A2 - Procede de preparation de carbamoyl-1 (dichloro-3,5-phenyl)-3 hydantoines - Google Patents
Procede de preparation de carbamoyl-1 (dichloro-3,5-phenyl)-3 hydantoines Download PDFInfo
- Publication number
- FR2504132A2 FR2504132A2 FR8107962A FR8107962A FR2504132A2 FR 2504132 A2 FR2504132 A2 FR 2504132A2 FR 8107962 A FR8107962 A FR 8107962A FR 8107962 A FR8107962 A FR 8107962A FR 2504132 A2 FR2504132 A2 FR 2504132A2
- Authority
- FR
- France
- Prior art keywords
- carbon atoms
- process according
- sep
- hydantoin
- radical
- 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.)
- Granted
Links
- 238000006243 chemical reaction Methods 0.000 title claims abstract description 9
- -1 chlorophenyl hydantoin Chemical compound 0.000 title claims description 46
- 125000001309 chloro group Chemical group Cl* 0.000 title claims description 5
- 150000001412 amines Chemical class 0.000 title abstract description 12
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 title abstract description 10
- 229940091173 hydantoin Drugs 0.000 title description 12
- NXQJDVBMMRCKQG-UHFFFAOYSA-N 5-phenylimidazolidine-2,4-dione Chemical compound O=C1NC(=O)NC1C1=CC=CC=C1 NXQJDVBMMRCKQG-UHFFFAOYSA-N 0.000 title 1
- 238000000034 method Methods 0.000 claims abstract description 25
- 239000002253 acid Substances 0.000 claims abstract description 13
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 28
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 17
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 14
- 239000002585 base Substances 0.000 claims description 12
- 239000003795 chemical substances by application Substances 0.000 claims description 8
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 8
- 239000011707 mineral Substances 0.000 claims description 8
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 7
- 238000012546 transfer Methods 0.000 claims description 6
- 239000012752 auxiliary agent Substances 0.000 claims description 5
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 claims description 5
- SHFJWMWCIHQNCP-UHFFFAOYSA-M tetrabutylammoniumhydrogensulfate Substances OS([O-])(=O)=O.CCCC[N+](CCCC)(CCCC)CCCC SHFJWMWCIHQNCP-UHFFFAOYSA-M 0.000 claims description 5
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 4
- 239000003153 chemical reaction reagent Substances 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000001453 quaternary ammonium group Chemical group 0.000 claims description 4
- 150000003254 radicals Chemical class 0.000 claims description 4
- 239000003352 sequestering agent Substances 0.000 claims description 4
- NHGXDBSUJJNIRV-UHFFFAOYSA-M tetrabutylammonium chloride Chemical group [Cl-].CCCC[N+](CCCC)(CCCC)CCCC NHGXDBSUJJNIRV-UHFFFAOYSA-M 0.000 claims description 4
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 3
- 239000000460 chlorine Substances 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 2
- 125000004423 acyloxy group Chemical group 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims description 2
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 2
- XGLVDUUYFKXKPL-UHFFFAOYSA-N 2-(2-methoxyethoxy)-n,n-bis[2-(2-methoxyethoxy)ethyl]ethanamine Chemical compound COCCOCCN(CCOCCOC)CCOCCOC XGLVDUUYFKXKPL-UHFFFAOYSA-N 0.000 claims 1
- 239000003513 alkali Substances 0.000 claims 1
- 125000005949 ethanesulfonyloxy group Chemical group 0.000 claims 1
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 claims 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 1
- 125000005496 phosphonium group Chemical group 0.000 claims 1
- 239000003960 organic solvent Substances 0.000 abstract description 5
- 239000000417 fungicide Substances 0.000 abstract description 3
- 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 description 3
- 238000004519 manufacturing process Methods 0.000 abstract description 2
- 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 2
- 230000000855 fungicidal effect Effects 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 16
- 239000007983 Tris buffer Substances 0.000 description 8
- 239000000203 mixture Substances 0.000 description 5
- 150000007530 organic bases Chemical class 0.000 description 5
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 238000009833 condensation Methods 0.000 description 4
- 230000005494 condensation Effects 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000004714 phosphonium salts Chemical class 0.000 description 3
- 229960000549 4-dimethylaminophenol Drugs 0.000 description 2
- 239000005867 Iprodione 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
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical compound CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
- WJRBRSLFGCUECM-UHFFFAOYSA-N hydantoin Chemical compound O=C1CNC(=O)N1 WJRBRSLFGCUECM-UHFFFAOYSA-N 0.000 description 2
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 239000012429 reaction media Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000003507 refrigerant Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-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
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000003849 aromatic solvent Substances 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000007872 degassing Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 125000005131 dialkylammonium group Chemical group 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000005647 linker group Chemical group 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- MFPXPCGVNXPRLZ-UHFFFAOYSA-N n-propan-2-ylcarbamoyl chloride Chemical compound CC(C)NC(Cl)=O MFPXPCGVNXPRLZ-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- IPOQVGGURGUZNU-UHFFFAOYSA-M tributyl(ethyl)azanium;chloride Chemical compound [Cl-].CCCC[N+](CC)(CCCC)CCCC IPOQVGGURGUZNU-UHFFFAOYSA-M 0.000 description 1
- IPILPUZVTYHGIL-UHFFFAOYSA-M tributyl(methyl)azanium;chloride Chemical compound [Cl-].CCCC[N+](C)(CCCC)CCCC IPILPUZVTYHGIL-UHFFFAOYSA-M 0.000 description 1
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (18)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8107962A FR2504132A2 (fr) | 1981-04-17 | 1981-04-17 | Procede de preparation de carbamoyl-1 (dichloro-3,5-phenyl)-3 hydantoines |
| AT81420079T ATE8625T1 (de) | 1980-05-29 | 1981-05-22 | Verfahren zur herstellung von 1-carbamoyl-3-(3,5- dichlorphenyl)-hydantoin und 1-chlorcarbonyl-3(3,5-dichlorphenyl)-hydantoin als zwischenprodukt in diesem verfahren. |
| EP81420079A EP0041465B1 (fr) | 1980-05-29 | 1981-05-22 | 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 |
| DE8181420079T DE3165038D1 (en) | 1980-05-29 | 1981-05-22 | Process for the preparation of 1-carbamoyl-3-(3,5-dichlorophenyl)-hydantoin, and 1-chlorocarbonyl-3-(3,5-dichlorophenyl) hydantoin as intermediate in this process |
| IL62946A IL62946A (en) | 1980-05-29 | 1981-05-25 | Process for the preparation of 1-carbamoyl-3-(3,5-dichlorophenyl)-hydantoin and the compound 1-chlorocarbonyl-3-(3,5-dichlorophenyl)-hydantoin as an intermediate in this process |
| RO81104414A RO82169A (ro) | 1980-05-29 | 1981-05-26 | Procedeu pentru prepararea 1-carbamoil-(3,5-diclor-denil)-3-hidantocinelor |
| IE1182/81A IE51269B1 (en) | 1980-05-29 | 1981-05-27 | Process for the preparation of 1-carbamoyl-3-(3,5-dichlorophenyl)-hydantoins and an intermediate therefor |
| DD81230338A DD159173A5 (de) | 1980-05-29 | 1981-05-27 | Verfahren zur herstellung von n-substituierten 1-carbamoyl-3-(3,55-dichlor-phenyl)-hydantoinen,sowie von 1-chlorcarbonyl-3-(3,5-dichlor phenyl)-hydantoin,das bei der herstellung dieser verbindungen als zwischenprodukt verwendbar ist |
| JP8070381A JPS5724367A (en) | 1980-05-29 | 1981-05-27 | Manufacture of 1-carbamoyl-3-(3,5-dichlorophenyl)- hydantoin and intermediate 1-chlorocarbonyl- 3-(3,5-dichlorophenyl)-hydantoin therefor |
| CA000378415A CA1164466A (en) | 1980-05-29 | 1981-05-27 | Process for the preparation of 1-carbamoyl-3-(3,5- dichlorophenyl)-hydantoins and an intermediate therefor |
| DK231981A DK231981A (da) | 1980-05-29 | 1981-05-27 | Fremgangsmaade til fremstilling af 1-carbamoyl-3-(3,5-dichlophhenyl)-hydantoiner samt det til denne fremgangsmaade anvendelige syntesemellemprodukt 1-chlorcarbonyl-3-(3,5-dichlorphenyl)-hydantoin |
| BR8103341A BR8103341A (pt) | 1980-05-29 | 1981-05-28 | Processo de preparacao de carbamoil-1(diloro-2,5-fenil)-3-hidan-toinas |
| HU811599A HU190367B (en) | 1980-05-29 | 1981-05-28 | Process for producing 1-carbamoyl-1,3-bracket-3,5-dichloro-phenyl-bracket closed-hidanthoines and the intermediate 1-chloro-carbonyl-3-bracket-3,5-dichloro-phenyl-bracket closed-hidanthoine |
| ES502559A ES8207154A1 (es) | 1980-05-29 | 1981-05-28 | Un procedimiento de preparacion de carbamoil-1-(dicloro-3,5 fenil)-3-hidantoinas sustituidas en n |
| YU1378/81A YU42404B (en) | 1980-05-29 | 1981-05-29 | Process for obtaining 1-carbamoyl-3-(3,5-dichlorophenyl)-hydantione |
| US06/554,382 US4479006A (en) | 1980-05-29 | 1983-11-22 | Process for the preparation of 1-carbamoyl-3-(3,5-dichlorophenyl)-hydantoins |
| JP60063162A JPS60237073A (ja) | 1980-05-29 | 1985-03-27 | １−クロロカルボニル−３−（３，５−ジクロフエニル）−ヒダントイン |
| DK325989A DK325989D0 (da) | 1980-05-29 | 1989-06-30 | 1-chlorcarbonyl-3-(3,5-dichlorphenyl)-hydantoin og fremgangsmaade til fremstilling af denne forbindelse |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8107962A FR2504132A2 (fr) | 1981-04-17 | 1981-04-17 | Procede de preparation de carbamoyl-1 (dichloro-3,5-phenyl)-3 hydantoines |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FR2504132A2 true FR2504132A2 (fr) | 1982-10-22 |
| FR2504132B2 FR2504132B2 (enExample) | 1983-05-20 |
Family
ID=9257635
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR8107962A Granted FR2504132A2 (fr) | 1980-05-29 | 1981-04-17 | Procede de preparation de carbamoyl-1 (dichloro-3,5-phenyl)-3 hydantoines |
Country Status (1)
| Country | Link |
|---|---|
| FR (1) | FR2504132A2 (enExample) |
-
1981
- 1981-04-17 FR FR8107962A patent/FR2504132A2/fr active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| FR2504132B2 (enExample) | 1983-05-20 |
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