HU193851B - Process for preparing 1-(chlorcarbonyl)-3-(3,5-dichlorphenyl)-hydantoin - Google Patents
Process for preparing 1-(chlorcarbonyl)-3-(3,5-dichlorphenyl)-hydantoin Download PDFInfo
- Publication number
- HU193851B HU193851B HU861004A HU100486A HU193851B HU 193851 B HU193851 B HU 193851B HU 861004 A HU861004 A HU 861004A HU 100486 A HU100486 A HU 100486A HU 193851 B HU193851 B HU 193851B
- Authority
- HU
- Hungary
- Prior art keywords
- hydantoin
- reaction
- formula
- phosgene
- process according
- Prior art date
Links
- LDDXFCOLOCZCTP-UHFFFAOYSA-N 3-(3,5-dichlorophenyl)-2,4-dioxoimidazolidine-1-carbonyl chloride Chemical compound O=C1N(C(=O)Cl)CC(=O)N1C1=CC(Cl)=CC(Cl)=C1 LDDXFCOLOCZCTP-UHFFFAOYSA-N 0.000 title claims 2
- 238000004519 manufacturing process Methods 0.000 title 1
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims abstract description 16
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims abstract description 14
- 238000006243 chemical reaction Methods 0.000 claims abstract description 11
- 239000002253 acid Substances 0.000 claims abstract description 10
- 239000003960 organic solvent Substances 0.000 claims abstract description 4
- 238000000034 method Methods 0.000 claims description 21
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical group CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 18
- 239000011541 reaction mixture Substances 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 8
- 239000002516 radical scavenger Substances 0.000 claims description 6
- 150000007529 inorganic bases Chemical group 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- -1 3,5-dichloro-phenyl Chemical group 0.000 claims description 3
- 125000001931 aliphatic group Chemical group 0.000 claims description 3
- 238000009835 boiling Methods 0.000 claims description 3
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 3
- 150000003512 tertiary amines Chemical group 0.000 claims description 3
- 239000011230 binding agent Substances 0.000 claims description 2
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims 1
- MVPPADPHJFYWMZ-IDEBNGHGSA-N chlorobenzene Chemical group Cl[13C]1=[13CH][13CH]=[13CH][13CH]=[13CH]1 MVPPADPHJFYWMZ-IDEBNGHGSA-N 0.000 claims 1
- 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 description 6
- 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 2
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 abstract description 2
- 150000001875 compounds Chemical class 0.000 description 9
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- 239000007788 liquid Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 150000007530 organic bases Chemical class 0.000 description 4
- 229960000549 4-dimethylaminophenol Drugs 0.000 description 3
- 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
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 229940091173 hydantoin Drugs 0.000 description 3
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 2
- 239000003849 aromatic solvent Substances 0.000 description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical compound CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- WJRBRSLFGCUECM-UHFFFAOYSA-N hydantoin Chemical compound O=C1CNC(=O)N1 WJRBRSLFGCUECM-UHFFFAOYSA-N 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
- 229910010272 inorganic material Inorganic materials 0.000 description 2
- 239000011147 inorganic material Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 2
- 238000003756 stirring 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
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 239000005867 Iprodione Substances 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 1
- 206010034962 Photopsia Diseases 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 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
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 238000002955 isolation Methods 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
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229910000065 phosphene Inorganic materials 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 125000005270 trialkylamine group Chemical group 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)
- 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 |
|---|---|
| HU193851B true HU193851B (en) | 1987-12-28 |
Family
ID=9242608
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU861004A HU193851B (en) | 1980-05-29 | 1981-05-28 | Process for preparing 1-(chlorcarbonyl)-3-(3,5-dichlorphenyl)-hydantoin |
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) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19622489A1 (de) * | 1996-06-05 | 1997-12-11 | Hoechst Ag | Salze des 3-(2-(4-(4-(Amino-imino-methyl)-phenyl)-4- methyl-2,5-dioxo-imidazolidin-1-yl)-acetylamino)-3- phenyl-propionsäure-ethylesters |
| DE19741235A1 (de) * | 1997-09-18 | 1999-03-25 | Hoechst Marion Roussel De Gmbh | Neue Imidazolidinderivate, ihre Herstellung, ihre Verwendung und sie enthaltende pharmazeutische Präparate |
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
Also Published As
| Publication number | Publication date |
|---|---|
| KR840001563B1 (ko) | 1984-10-05 |
| FR2483414A1 (fr) | 1981-12-04 |
| KR830006227A (ko) | 1983-09-20 |
| SU1318157A3 (ru) | 1987-06-15 |
| ZA813601B (en) | 1982-06-30 |
| FR2483414B1 (enExample) | 1982-11-12 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| HU90 | Patent valid on 900628 | ||
| HMM4 | Cancellation of final prot. due to non-payment of fee |