CA1127183A - Procede de dedoublement des acides dl-cis et dl-trans-2,2-dimethyl-3-(2',2'-dihalovinyl) cyclopropane-1-carboxylique - Google Patents
Procede de dedoublement des acides dl-cis et dl-trans-2,2-dimethyl-3-(2',2'-dihalovinyl) cyclopropane-1-carboxyliqueInfo
- Publication number
- CA1127183A CA1127183A CA348,882A CA348882A CA1127183A CA 1127183 A CA1127183 A CA 1127183A CA 348882 A CA348882 A CA 348882A CA 1127183 A CA1127183 A CA 1127183A
- Authority
- CA
- Canada
- Prior art keywords
- acid
- ephedrine
- dimethyl
- cis
- carboxylic
- 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 53
- YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical class OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 title claims abstract description 17
- 239000002253 acid Substances 0.000 claims abstract description 111
- KWGRBVOPPLSCSI-WPRPVWTQSA-N (-)-ephedrine Chemical compound CN[C@@H](C)[C@H](O)C1=CC=CC=C1 KWGRBVOPPLSCSI-WPRPVWTQSA-N 0.000 claims abstract description 60
- 150000003839 salts Chemical class 0.000 claims abstract description 49
- KWGRBVOPPLSCSI-UHFFFAOYSA-N d-ephedrine Natural products CNC(C)C(O)C1=CC=CC=C1 KWGRBVOPPLSCSI-UHFFFAOYSA-N 0.000 claims abstract description 37
- 238000005903 acid hydrolysis reaction Methods 0.000 claims abstract description 23
- 229960002221 methylephedrine Drugs 0.000 claims abstract description 19
- 229960002179 ephedrine Drugs 0.000 claims abstract description 15
- KWGRBVOPPLSCSI-SCZZXKLOSA-N (1r,2r)-2-(methylamino)-1-phenylpropan-1-ol Chemical compound CN[C@H](C)[C@H](O)C1=CC=CC=C1 KWGRBVOPPLSCSI-SCZZXKLOSA-N 0.000 claims abstract description 10
- 150000007513 acids Chemical class 0.000 claims abstract description 8
- KWGRBVOPPLSCSI-WCBMZHEXSA-N pseudoephedrine Chemical compound CN[C@@H](C)[C@@H](O)C1=CC=CC=C1 KWGRBVOPPLSCSI-WCBMZHEXSA-N 0.000 claims abstract description 8
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 5
- 229910052794 bromium Chemical group 0.000 claims abstract description 5
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 5
- 239000000460 chlorine Chemical group 0.000 claims abstract description 5
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 5
- 239000011737 fluorine Substances 0.000 claims abstract description 5
- 125000001153 fluoro group Chemical group F* 0.000 claims abstract description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 28
- -1 2,2-dibromovinyl Chemical group 0.000 claims description 22
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 21
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 21
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 claims description 20
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 18
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 18
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 16
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 15
- 238000006243 chemical reaction Methods 0.000 claims description 15
- 239000000203 mixture Substances 0.000 claims description 12
- 239000002904 solvent Substances 0.000 claims description 9
- LLMLSUSAKZVFOA-UHFFFAOYSA-N 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylic acid Chemical compound CC1(C)C(C=C(Cl)Cl)C1C(O)=O LLMLSUSAKZVFOA-UHFFFAOYSA-N 0.000 claims description 7
- MDIQXIJPQWLFSD-UHFFFAOYSA-N 3-(2,2-dibromoethenyl)-2,2-dimethylcyclopropane-1-carboxylic acid Chemical compound CC1(C)C(C=C(Br)Br)C1C(O)=O MDIQXIJPQWLFSD-UHFFFAOYSA-N 0.000 claims description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 6
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 claims description 5
- YUACDUKFVCTPKB-UHFFFAOYSA-N 2-(2,2-dichloroethenyl)cyclopropane-1-carboxylic acid Chemical compound OC(=O)C1CC1C=C(Cl)Cl YUACDUKFVCTPKB-UHFFFAOYSA-N 0.000 claims description 3
- 229940073569 n-methylephedrine Drugs 0.000 claims description 3
- FMCGSUUBYTWNDP-ONGXEEELSA-N (1R,2S)-2-(dimethylamino)-1-phenyl-1-propanol Chemical compound CN(C)[C@@H](C)[C@H](O)C1=CC=CC=C1 FMCGSUUBYTWNDP-ONGXEEELSA-N 0.000 claims description 2
- VNHCVSAJTOUUBK-UHFFFAOYSA-N 1-(2,2-dichloroethenyl)cyclopropane-1-carboxylic acid Chemical compound ClC(Cl)=CC1(C(=O)O)CC1 VNHCVSAJTOUUBK-UHFFFAOYSA-N 0.000 claims description 2
- FMCGSUUBYTWNDP-UHFFFAOYSA-N N-Methylephedrine Natural products CN(C)C(C)C(O)C1=CC=CC=C1 FMCGSUUBYTWNDP-UHFFFAOYSA-N 0.000 claims description 2
- HIJYQGOHEVMVFO-UHFFFAOYSA-N 2-(2,2-dibromoethenyl)cyclopropane-1-carboxylic acid Chemical compound OC(=O)C1CC1C=C(Br)Br HIJYQGOHEVMVFO-UHFFFAOYSA-N 0.000 claims 1
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims 1
- 241000209140 Triticum Species 0.000 claims 1
- 235000021307 Triticum Nutrition 0.000 claims 1
- 239000013078 crystal Substances 0.000 claims 1
- 238000002425 crystallisation Methods 0.000 claims 1
- 230000008025 crystallization Effects 0.000 claims 1
- 230000009089 cytolysis Effects 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 abstract description 2
- 150000002148 esters Chemical class 0.000 abstract description 2
- 230000000749 insecticidal effect Effects 0.000 abstract description 2
- 238000003786 synthesis reaction Methods 0.000 abstract description 2
- 239000000543 intermediate Substances 0.000 abstract 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 39
- 230000007062 hydrolysis Effects 0.000 description 11
- 238000006460 hydrolysis reaction Methods 0.000 description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- RHMQNXNXUZLEIY-UHFFFAOYSA-N methanol;2-propan-2-yloxypropane Chemical compound OC.CC(C)OC(C)C RHMQNXNXUZLEIY-UHFFFAOYSA-N 0.000 description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- PYQUFDITSDHLQE-UHFFFAOYSA-N 1-(2,2-dibromoethenyl)cyclopropane-1-carboxylic acid Chemical compound BrC(Br)=CC1(C(=O)O)CC1 PYQUFDITSDHLQE-UHFFFAOYSA-N 0.000 description 1
- CUACAHUDGBWTME-UHFFFAOYSA-N 2-(dimethylamino)propane-1,3-diol Chemical compound CN(C)C(CO)CO CUACAHUDGBWTME-UHFFFAOYSA-N 0.000 description 1
- VGKZBAMIYUHSMU-UHFFFAOYSA-N 4-[[2-chloroethyl(nitroso)carbamoyl]amino]cyclohexane-1-carboxylic acid Chemical compound OC(=O)C1CCC(NC(=O)N(CCCl)N=O)CC1 VGKZBAMIYUHSMU-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- WBIBIAFMCVDEIN-UHFFFAOYSA-N C1C[ClH][ClH]1 Chemical compound C1C[ClH][ClH]1 WBIBIAFMCVDEIN-UHFFFAOYSA-N 0.000 description 1
- 241001560893 Cycloes Species 0.000 description 1
- LVZWSLJZHVFIQJ-UHFFFAOYSA-N Cyclopropane Chemical compound C1CC1 LVZWSLJZHVFIQJ-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- MCRWZBYTLVCCJJ-DKALBXGISA-N [(1s,3r)-3-[[(3s,4s)-3-methoxyoxan-4-yl]amino]-1-propan-2-ylcyclopentyl]-[(1s,4s)-5-[6-(trifluoromethyl)pyrimidin-4-yl]-2,5-diazabicyclo[2.2.1]heptan-2-yl]methanone Chemical compound C([C@]1(N(C[C@]2([H])C1)C(=O)[C@@]1(C[C@@H](CC1)N[C@@H]1[C@@H](COCC1)OC)C(C)C)[H])N2C1=CC(C(F)(F)F)=NC=N1 MCRWZBYTLVCCJJ-DKALBXGISA-N 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 125000000950 dibromo group Chemical group Br* 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 229960003908 pseudoephedrine Drugs 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 238000005063 solubilization Methods 0.000 description 1
- 230000007928 solubilization Effects 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
- C07C51/487—Separation; Purification; Stabilisation; Use of additives by treatment giving rise to chemical modification
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7908338A FR2455024A1 (fr) | 1979-04-03 | 1979-04-03 | Nouveau procede de dedoublement des acides d,l-cis 2,2-dimethyl 3-(2',2'-dihalovinyl) cyclopropane-1-carboxylique |
| FR79-08338 | 1979-04-03 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1127183A true CA1127183A (fr) | 1982-07-06 |
Family
ID=9223879
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA348,882A Expired CA1127183A (fr) | 1979-04-03 | 1980-03-31 | Procede de dedoublement des acides dl-cis et dl-trans-2,2-dimethyl-3-(2',2'-dihalovinyl) cyclopropane-1-carboxylique |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US4328173A (en, 2012) |
| JP (2) | JPS55133330A (en, 2012) |
| BE (1) | BE882595A (en, 2012) |
| CA (1) | CA1127183A (en, 2012) |
| CH (1) | CH648284A5 (en, 2012) |
| DE (2) | DE3013151A1 (en, 2012) |
| ES (1) | ES489922A1 (en, 2012) |
| FR (1) | FR2455024A1 (en, 2012) |
| GB (1) | GB2047696B (en, 2012) |
| HU (1) | HU185212B (en, 2012) |
| IT (1) | IT1144044B (en, 2012) |
| NL (1) | NL192681C (en, 2012) |
| SE (1) | SE447822B (en, 2012) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HU185030B (en) * | 1981-02-20 | 1984-11-28 | Chinoin Gyogyszer Es Vegyeszet | Process for producing isomere mixtures of pure dichloro-vinyl-cyclopropane-carboxylic acids |
| AU543276B2 (en) * | 1981-06-18 | 1985-04-18 | Stauffer Chemical Company | Resolution of dl-trans-chrysanthemic acid |
| HU188335B (en) * | 1982-11-25 | 1986-04-28 | Chinoin Gyogyszer Es Vegyeszeti Termekek Gyara Rt,Hu | Process for preparing optically active derivatives of cyclopropane-carboxylic acid |
| JPH02131883U (en, 2012) * | 1989-04-04 | 1990-11-01 | ||
| GB2330579B (en) * | 1997-10-31 | 1999-09-08 | Gharda Chemicals Limited | Resolution of the (+)2,2-dimethyl-3-(2,2-disubstitutedvinyl)-cyclopropane-1-carboxylic acids from its optical Isomers |
| ITMI20050231A1 (it) * | 2005-02-17 | 2006-08-18 | Endura Spa | Processo per l'ottenimento di enantiomeri dell'acido crisantemico |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3590077A (en) * | 1966-01-26 | 1971-06-29 | Roussel Uclaf | Salts of chrysanthemic acid with 1-p-nitrophenyl - 2-n,n - dimethyl-aminopropane-1,3-diols |
| FR1507192A (fr) * | 1966-08-26 | 1967-12-29 | Roussel Uclaf | Nouvelles aryl allylsulfones et procédé de préparation |
| US4014918A (en) * | 1968-07-12 | 1977-03-29 | Roussel-Uclaf | Process for the preparation of cyclopropane derivatives and compounds produced therein |
| US3739019A (en) * | 1969-07-02 | 1973-06-12 | Sumitomo Chemical Co | Preparation of optically active trans chrysanthemic acid |
| BE790240A (fr) * | 1971-10-19 | 1973-02-15 | Sumitomo Chemical Co | Procede de preparation de l'acide mixte (+)-cis, (+)-trans- chrysanthemique |
| JPS5123497B2 (en, 2012) * | 1972-01-07 | 1976-07-17 | ||
| US4024163A (en) * | 1972-05-25 | 1977-05-17 | National Research Development Corporation | Insecticides |
| IE41614B1 (en) * | 1973-08-15 | 1980-02-13 | Nat Res Dev | Substituted 2,2-dimethyl cylopropane carboxylic acid estersprocess for their preperation and their use as insecticides |
| JPS562060B2 (en, 2012) * | 1974-04-09 | 1981-01-17 | ||
| JPS5136441A (en) * | 1974-09-20 | 1976-03-27 | Sumitomo Chemical Co | * purasu * toransu 2*22 jimechiru 33 * 2*22 jikurorubiniru * shikuroburopankarubonsannoshutokuhoho |
| JPS51143647A (en) * | 1975-06-06 | 1976-12-10 | Sumitomo Chem Co Ltd | Process for obtaining optically active trans-2,2-dimethyl-3-(2,2-dichl orovinyl) cyclopropanecarboxylic acid |
| DE2826952A1 (de) * | 1978-06-20 | 1980-01-10 | Bayer Ag | Enantiomerentrennung von chiralen carbonsaeuren |
| US4229593A (en) * | 1979-05-29 | 1980-10-21 | Fmc Corporation | Method to prepare (+)-cis-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylic acid |
-
1979
- 1979-04-03 FR FR7908338A patent/FR2455024A1/fr active Granted
-
1980
- 1980-01-30 SE SE8000740A patent/SE447822B/sv not_active IP Right Cessation
- 1980-01-31 HU HU80208A patent/HU185212B/hu not_active IP Right Cessation
- 1980-03-10 IT IT48118/80A patent/IT1144044B/it active
- 1980-03-17 US US06/130,994 patent/US4328173A/en not_active Expired - Lifetime
- 1980-03-26 ES ES489922A patent/ES489922A1/es not_active Expired
- 1980-03-31 CA CA348,882A patent/CA1127183A/fr not_active Expired
- 1980-04-01 JP JP4125080A patent/JPS55133330A/ja active Granted
- 1980-04-02 NL NL8001953A patent/NL192681C/nl not_active IP Right Cessation
- 1980-04-02 GB GB8011160A patent/GB2047696B/en not_active Expired
- 1980-04-02 CH CH2625/80A patent/CH648284A5/fr not_active IP Right Cessation
- 1980-04-02 BE BE0/200085A patent/BE882595A/fr not_active IP Right Cessation
- 1980-04-03 DE DE19803013151 patent/DE3013151A1/de active Granted
- 1980-04-03 DE DE3051212A patent/DE3051212C2/de not_active Expired - Fee Related
-
1988
- 1988-12-07 JP JP63307958A patent/JPH02134A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| GB2047696B (en) | 1983-04-20 |
| IT8048118A0 (it) | 1980-03-10 |
| JPS55133330A (en) | 1980-10-17 |
| NL192681C (nl) | 1997-12-02 |
| NL8001953A (nl) | 1980-10-07 |
| US4328173A (en) | 1982-05-04 |
| CH648284A5 (fr) | 1985-03-15 |
| GB2047696A (en) | 1980-12-03 |
| DE3051212C2 (en, 2012) | 1991-06-27 |
| FR2455024A1 (fr) | 1980-11-21 |
| FR2455024B1 (en, 2012) | 1981-10-02 |
| SE447822B (sv) | 1986-12-15 |
| HU185212B (en) | 1984-12-28 |
| IT1144044B (it) | 1986-10-29 |
| SE8000740L (sv) | 1980-10-04 |
| NL192681B (nl) | 1997-08-01 |
| DE3013151A1 (de) | 1980-10-23 |
| DE3013151C2 (en, 2012) | 1990-10-11 |
| JPH0134979B2 (en, 2012) | 1989-07-21 |
| JPH02134A (ja) | 1990-01-05 |
| JPH0314818B2 (en, 2012) | 1991-02-27 |
| BE882595A (fr) | 1980-10-02 |
| ES489922A1 (es) | 1980-10-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |