JPS6019299B2 - １−カルバモイル−３−（３，５−ジクロロ−フエニル）−ヒダントインの製法 - Google Patents
１−カルバモイル−３−（３，５−ジクロロ−フエニル）−ヒダントインの製法Info
- Publication number
- JPS6019299B2 JPS6019299B2 JP51017441A JP1744176A JPS6019299B2 JP S6019299 B2 JPS6019299 B2 JP S6019299B2 JP 51017441 A JP51017441 A JP 51017441A JP 1744176 A JP1744176 A JP 1744176A JP S6019299 B2 JPS6019299 B2 JP S6019299B2
- Authority
- JP
- Japan
- Prior art keywords
- hydantoin
- production method
- organic solvent
- dichlorophenyl
- dichloro
- 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 description 13
- 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 title claims 2
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical group CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 33
- 238000006243 chemical reaction Methods 0.000 claims description 17
- 239000012948 isocyanate Substances 0.000 claims description 12
- 150000002513 isocyanates Chemical class 0.000 claims description 12
- 238000004519 manufacturing process Methods 0.000 claims description 12
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Substances ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 9
- 239000002904 solvent Substances 0.000 claims description 9
- 239000003960 organic solvent Substances 0.000 claims description 7
- 150000003512 tertiary amines Chemical class 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 3
- 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 claims description 2
- 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
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000005270 trialkylamine group Chemical group 0.000 claims description 2
- MVPPADPHJFYWMZ-IDEBNGHGSA-N chlorobenzene Chemical group Cl[13C]1=[13CH][13CH]=[13CH][13CH]=[13CH]1 MVPPADPHJFYWMZ-IDEBNGHGSA-N 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 125000000468 ketone group Chemical group 0.000 claims 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- 239000011541 reaction mixture Substances 0.000 description 11
- 239000002244 precipitate Substances 0.000 description 9
- 239000000725 suspension Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 238000001816 cooling Methods 0.000 description 7
- 239000012153 distilled water Substances 0.000 description 7
- 239000000155 melt Substances 0.000 description 7
- GSLTVFIVJMCNBH-UHFFFAOYSA-N 2-isocyanatopropane Chemical compound CC(C)N=C=O GSLTVFIVJMCNBH-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 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 description 6
- 239000000047 product Substances 0.000 description 6
- 238000010992 reflux Methods 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 150000008064 anhydrides Chemical class 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 229940091173 hydantoin Drugs 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 2
- KZVRXPPUJQRGFN-UHFFFAOYSA-N N-carbamoylglycine Chemical compound NC(=O)NCC(O)=O KZVRXPPUJQRGFN-UHFFFAOYSA-N 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 238000007363 ring formation reaction Methods 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 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
- BMVXCPBXGZKUPN-UHFFFAOYSA-N 1-hexanamine Chemical compound CCCCCCN BMVXCPBXGZKUPN-UHFFFAOYSA-N 0.000 description 1
- OQURWGJAWSLGQG-UHFFFAOYSA-N 1-isocyanatopropane Chemical compound CCCN=C=O OQURWGJAWSLGQG-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- -1 3,5-dichlorophenyl Chemical group 0.000 description 1
- KDUAVSLSEYRQRB-UHFFFAOYSA-N 3-(3,5-dichlorophenyl)-2,4-dioxo-n-propylimidazolidine-1-carboxamide Chemical compound O=C1N(C(=O)NCCC)CC(=O)N1C1=CC(Cl)=CC(Cl)=C1 KDUAVSLSEYRQRB-UHFFFAOYSA-N 0.000 description 1
- JRLTTZUODKEYDH-UHFFFAOYSA-N 8-methylquinoline Chemical group C1=CN=C2C(C)=CC=CC2=C1 JRLTTZUODKEYDH-UHFFFAOYSA-N 0.000 description 1
- 239000004471 Glycine Substances 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- FAUVWSCAPAZACA-UHFFFAOYSA-N [N]NC(N)=O Chemical compound [N]NC(N)=O FAUVWSCAPAZACA-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 239000003849 aromatic solvent Substances 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- WJRBRSLFGCUECM-UHFFFAOYSA-N hydantoin Chemical compound O=C1CNC(=O)N1 WJRBRSLFGCUECM-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 235000013555 soy sauce Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
- RKBCYCFRFCNLTO-UHFFFAOYSA-N triisopropylamine Chemical compound CC(C)N(C(C)C)C(C)C RKBCYCFRFCNLTO-UHFFFAOYSA-N 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
- 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)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7539905A FR2336397A1 (fr) | 1975-12-22 | 1975-12-22 | Nouveau procede de preparation de carbamoyl-i (dichloro-3,5 phenyl)-3 hydantoines |
| FR000007539905 | 1975-12-22 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5278872A JPS5278872A (en) | 1977-07-02 |
| JPS6019299B2 true JPS6019299B2 (ja) | 1985-05-15 |
Family
ID=9164226
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP51017441A Expired JPS6019299B2 (ja) | 1975-12-22 | 1976-02-18 | １−カルバモイル−３−（３，５−ジクロロ−フエニル）−ヒダントインの製法 |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US4076941A (OSRAM) |
| JP (1) | JPS6019299B2 (OSRAM) |
| AT (1) | AT347969B (OSRAM) |
| BE (1) | BE849686A (OSRAM) |
| CH (1) | CH618689A5 (OSRAM) |
| DE (1) | DE2658220C2 (OSRAM) |
| FR (1) | FR2336397A1 (OSRAM) |
| GB (1) | GB1505050A (OSRAM) |
| IL (1) | IL51140A (OSRAM) |
| IT (1) | IT1065700B (OSRAM) |
| NL (1) | NL7614218A (OSRAM) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2750772A1 (de) * | 1977-11-12 | 1979-05-17 | Bayer Ag | Heterocyclische polyisocyanate (iii) |
| US4746755A (en) * | 1986-05-06 | 1988-05-24 | The Dow Chemical Company | Preparation of hydrantoic acids and hydantoins |
| AR102942A1 (es) | 2014-12-11 | 2017-04-05 | Bayer Cropscience Ag | Derivados de arilsulfuro y arilsulfóxido de cinco miembros c-n-conectados, como plaguicidas |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2829157A (en) * | 1953-03-10 | 1958-04-01 | Leonard L Mckinney | Novel hydantoic acids and their alkyl esters |
| FR2148868A6 (OSRAM) * | 1970-10-06 | 1973-03-23 | Rhone Poulenc Sa | |
| FR2120222A5 (en) * | 1970-10-06 | 1972-08-18 | Rhone Poulenc Sa | N-acyl-hydantoin derivs - with fungicidal activity |
| GB1472467A (en) * | 1974-04-19 | 1977-05-04 | Wyeth John & Brother Ltd | Thiohydantoins |
-
1975
- 1975-12-22 FR FR7539905A patent/FR2336397A1/fr active Granted
-
1976
- 1976-02-18 JP JP51017441A patent/JPS6019299B2/ja not_active Expired
- 1976-12-15 US US05/750,704 patent/US4076941A/en not_active Expired - Lifetime
- 1976-12-20 GB GB53157/76A patent/GB1505050A/en not_active Expired
- 1976-12-21 BE BE173494A patent/BE849686A/xx not_active IP Right Cessation
- 1976-12-21 CH CH1611876A patent/CH618689A5/fr not_active IP Right Cessation
- 1976-12-21 NL NL7614218A patent/NL7614218A/xx not_active Application Discontinuation
- 1976-12-21 IL IL51140A patent/IL51140A/xx unknown
- 1976-12-22 AT AT956476A patent/AT347969B/de not_active IP Right Cessation
- 1976-12-22 DE DE2658220A patent/DE2658220C2/de not_active Expired
- 1976-12-22 IT IT30766/76A patent/IT1065700B/it active
Also Published As
| Publication number | Publication date |
|---|---|
| FR2336397A1 (fr) | 1977-07-22 |
| DE2658220A1 (de) | 1977-06-23 |
| IT1065700B (it) | 1985-03-04 |
| CH618689A5 (OSRAM) | 1980-08-15 |
| IL51140A (en) | 1980-06-30 |
| AT347969B (de) | 1979-01-25 |
| BE849686A (fr) | 1977-06-21 |
| ATA956476A (de) | 1978-06-15 |
| GB1505050A (en) | 1978-03-22 |
| JPS5278872A (en) | 1977-07-02 |
| IL51140A0 (en) | 1977-02-28 |
| NL7614218A (nl) | 1977-06-24 |
| US4076941A (en) | 1978-02-28 |
| FR2336397B1 (OSRAM) | 1978-12-08 |
| DE2658220C2 (de) | 1986-09-18 |
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