CA1067502A - Process for the preparation of 3-(3,5-dichlorophenyl)-hydantoin - Google Patents
Process for the preparation of 3-(3,5-dichlorophenyl)-hydantoinInfo
- Publication number
- CA1067502A CA1067502A CA258,857A CA258857A CA1067502A CA 1067502 A CA1067502 A CA 1067502A CA 258857 A CA258857 A CA 258857A CA 1067502 A CA1067502 A CA 1067502A
- Authority
- CA
- Canada
- Prior art keywords
- acid
- dichlorophenyl
- dehydrating agent
- hydantoin
- ureidoacetic
- 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
- 238000000034 method Methods 0.000 title claims abstract description 11
- 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 title claims abstract description 10
- 238000002360 preparation method Methods 0.000 title claims abstract description 7
- 239000002253 acid Substances 0.000 claims abstract description 13
- 239000012024 dehydrating agents Substances 0.000 claims abstract description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 11
- KZVRXPPUJQRGFN-UHFFFAOYSA-N N-carbamoylglycine Chemical group NC(=O)NCC(O)=O KZVRXPPUJQRGFN-UHFFFAOYSA-N 0.000 claims abstract description 9
- LUTUCNIKEYNGLK-UHFFFAOYSA-N 2-[(3,5-dichlorophenyl)carbamoylamino]acetic acid Chemical compound OC(=O)CNC(=O)NC1=CC(Cl)=CC(Cl)=C1 LUTUCNIKEYNGLK-UHFFFAOYSA-N 0.000 claims abstract description 8
- 239000003960 organic solvent Substances 0.000 claims abstract description 5
- 230000003197 catalytic effect Effects 0.000 claims abstract description 4
- 239000007858 starting material Substances 0.000 claims abstract description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Substances ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 9
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical group OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 5
- 239000001117 sulphuric acid Substances 0.000 claims description 5
- 235000011149 sulphuric acid Nutrition 0.000 claims description 5
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 4
- 238000010533 azeotropic distillation Methods 0.000 claims description 4
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 claims description 4
- MVPPADPHJFYWMZ-IDEBNGHGSA-N chlorobenzene Chemical group Cl[13C]1=[13CH][13CH]=[13CH][13CH]=[13CH]1 MVPPADPHJFYWMZ-IDEBNGHGSA-N 0.000 claims 1
- 238000004821 distillation Methods 0.000 abstract description 5
- 230000000855 fungicidal effect Effects 0.000 abstract description 2
- 239000000417 fungicide Substances 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
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- WJRBRSLFGCUECM-UHFFFAOYSA-N hydantoin Chemical compound O=C1CNC(=O)N1 WJRBRSLFGCUECM-UHFFFAOYSA-N 0.000 description 3
- 229940091173 hydantoin Drugs 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 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
- 239000004471 Glycine Substances 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
- 239000003377 acid catalyst Substances 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000008422 chlorobenzenes Chemical class 0.000 description 1
- JEVCWSUVFOYBFI-UHFFFAOYSA-N cyanyl Chemical compound N#[C] JEVCWSUVFOYBFI-UHFFFAOYSA-N 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical compound O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 150000003672 ureas Chemical class 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7525209A FR2320945A1 (fr) | 1975-08-13 | 1975-08-13 | Nouveau procede de preparation de la (dichloro-3,5 phenyl)-3 hydantoine |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1067502A true CA1067502A (en) | 1979-12-04 |
Family
ID=9159049
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA258,857A Expired CA1067502A (en) | 1975-08-13 | 1976-08-11 | Process for the preparation of 3-(3,5-dichlorophenyl)-hydantoin |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US4099008A (forum.php) |
| JP (1) | JPS5227769A (forum.php) |
| AT (1) | AT346360B (forum.php) |
| BE (1) | BE845131A (forum.php) |
| BR (1) | BR7605274A (forum.php) |
| CA (1) | CA1067502A (forum.php) |
| CH (1) | CH608491A5 (forum.php) |
| DD (1) | DD126510A5 (forum.php) |
| DE (1) | DE2636549C2 (forum.php) |
| FR (1) | FR2320945A1 (forum.php) |
| GB (1) | GB1501527A (forum.php) |
| IE (1) | IE43522B1 (forum.php) |
| IL (1) | IL50247A (forum.php) |
| IT (1) | IT1065785B (forum.php) |
| LU (1) | LU75581A1 (forum.php) |
| NL (1) | NL189857C (forum.php) |
| SU (1) | SU612626A3 (forum.php) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103539744B (zh) * | 2013-10-17 | 2016-03-23 | 北京颖泰嘉和生物科技股份有限公司 | 一种制备3-(3,5-二氯苯基)-2,4-咪唑烷二酮的方法 |
| CN105777647B (zh) * | 2016-04-06 | 2018-06-01 | 江苏快达农化股份有限公司 | 一种合成1-异丙基氨基甲酰胺-3-(3,5-二氯苯基)乙内酰脲的方法 |
| CN107245055B (zh) * | 2017-06-07 | 2020-02-14 | 江苏蓝丰生物化工股份有限公司 | 异菌脲的制备方法 |
| JP7131463B2 (ja) | 2019-04-02 | 2022-09-06 | トヨタ自動車株式会社 | 燃料電池システム |
| CN117945952A (zh) * | 2024-01-02 | 2024-04-30 | 江西禾益化工股份有限公司 | 一种制备1-羧甲基-3-(3,5-二氯苯基)脲的方法 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3395153A (en) * | 1964-12-16 | 1968-07-30 | United States Borax Chem | 3, 5-dialkylhydantoins |
| FR1074999A (fr) * | 1964-12-16 | 1954-10-11 | Paul Hug Ets | Appareil pour le contrôle de la hauteur des dents de scies et outils similaires |
| US3448116A (en) * | 1966-04-25 | 1969-06-03 | American Home Prod | Preparation of 1-hydroxyhydantoins and 1-hydroxythiohydantoins |
| DK123717B (da) * | 1968-11-25 | 1972-07-24 | Sumitomo Chemical Co | 3-(3',5'-Dihalogenphenyl)-imidazolidin-2,4-dionderivater med mirobicid virkning. |
| DE1906492B2 (de) * | 1969-02-10 | 1980-07-31 | Bayer Ag, 5090 Leverkusen | Carbonsäure-Derivate enthaltende Hydantoine und Polyhydantoine |
| US3814776A (en) * | 1969-02-21 | 1974-06-04 | Bayer Ag | Hydantoins and polyhydantoins containing olefin groups |
| US3676456A (en) * | 1970-02-27 | 1972-07-11 | Ciba Geigy Corp | Derivatives of 3-aryl-5-alkylhydantoins |
| FR2120222A5 (en) * | 1970-10-06 | 1972-08-18 | Rhone Poulenc Sa | N-acyl-hydantoin derivs - with fungicidal activity |
| FR2148868A6 (forum.php) * | 1970-10-06 | 1973-03-23 | Rhone Poulenc Sa |
-
1975
- 1975-08-13 FR FR7525209A patent/FR2320945A1/fr active Granted
-
1976
- 1976-08-10 IE IE1769/76A patent/IE43522B1/en not_active IP Right Cessation
- 1976-08-11 SU SU762386165A patent/SU612626A3/ru active
- 1976-08-11 CA CA258,857A patent/CA1067502A/en not_active Expired
- 1976-08-12 BE BE169764A patent/BE845131A/xx not_active IP Right Cessation
- 1976-08-12 US US05/713,638 patent/US4099008A/en not_active Expired - Lifetime
- 1976-08-12 NL NLAANVRAGE7608980,A patent/NL189857C/xx not_active IP Right Cessation
- 1976-08-12 AT AT600076A patent/AT346360B/de not_active IP Right Cessation
- 1976-08-12 BR BR7605274A patent/BR7605274A/pt unknown
- 1976-08-12 IL IL50247A patent/IL50247A/xx unknown
- 1976-08-12 JP JP51096875A patent/JPS5227769A/ja active Granted
- 1976-08-12 DD DD194304A patent/DD126510A5/xx unknown
- 1976-08-12 GB GB33665/76A patent/GB1501527A/en not_active Expired
- 1976-08-12 CH CH1029976A patent/CH608491A5/xx not_active IP Right Cessation
- 1976-08-12 LU LU75581A patent/LU75581A1/xx unknown
- 1976-08-13 DE DE2636549A patent/DE2636549C2/de not_active Expired
- 1976-08-13 IT IT26281/76A patent/IT1065785B/it active
Also Published As
| Publication number | Publication date |
|---|---|
| IL50247A (en) | 1980-01-31 |
| LU75581A1 (forum.php) | 1978-04-13 |
| DE2636549C2 (de) | 1986-08-21 |
| GB1501527A (en) | 1978-02-15 |
| FR2320945B1 (forum.php) | 1977-12-16 |
| SU612626A3 (ru) | 1978-06-25 |
| BR7605274A (pt) | 1977-08-09 |
| NL7608980A (nl) | 1977-02-15 |
| DD126510A5 (forum.php) | 1977-07-20 |
| FR2320945A1 (fr) | 1977-03-11 |
| BE845131A (fr) | 1977-02-14 |
| NL189857C (nl) | 1993-08-16 |
| IL50247A0 (en) | 1976-10-31 |
| DE2636549A1 (de) | 1977-02-24 |
| JPS5227769A (en) | 1977-03-02 |
| IT1065785B (it) | 1985-03-04 |
| CH608491A5 (forum.php) | 1979-01-15 |
| IE43522B1 (en) | 1981-03-25 |
| NL189857B (nl) | 1993-03-16 |
| ATA600076A (de) | 1978-03-15 |
| JPS5422979B2 (forum.php) | 1979-08-10 |
| US4099008A (en) | 1978-07-04 |
| AT346360B (de) | 1978-11-10 |
| IE43522L (en) | 1977-02-13 |
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