CH653012A5 - Verfahren zur stereospezifischen herstellung von 1-cyano-2(2,2-dihalogenvinyl)-3,3-dimethylcyclopropan. - Google Patents
Verfahren zur stereospezifischen herstellung von 1-cyano-2(2,2-dihalogenvinyl)-3,3-dimethylcyclopropan. Download PDFInfo
- Publication number
- CH653012A5 CH653012A5 CH4727/82A CH472782A CH653012A5 CH 653012 A5 CH653012 A5 CH 653012A5 CH 4727/82 A CH4727/82 A CH 4727/82A CH 472782 A CH472782 A CH 472782A CH 653012 A5 CH653012 A5 CH 653012A5
- Authority
- CH
- Switzerland
- Prior art keywords
- decarboxylation
- carboxylic acid
- trans
- acid
- compound
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 28
- 238000004519 manufacturing process Methods 0.000 title claims 2
- 230000000707 stereoselective effect Effects 0.000 title claims 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 19
- 238000006243 chemical reaction Methods 0.000 claims description 18
- 150000001875 compounds Chemical class 0.000 claims description 16
- 239000002253 acid Substances 0.000 claims description 14
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 14
- 238000006114 decarboxylation reaction Methods 0.000 claims description 14
- 150000003839 salts Chemical class 0.000 claims description 12
- 238000011065 in-situ storage Methods 0.000 claims description 6
- 150000001408 amides Chemical class 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 239000000460 chlorine Substances 0.000 claims description 5
- 230000007062 hydrolysis Effects 0.000 claims description 5
- 238000006460 hydrolysis reaction Methods 0.000 claims description 5
- 241000251730 Chondrichthyes Species 0.000 claims description 4
- 150000001879 copper Chemical class 0.000 claims description 4
- 239000012433 hydrogen halide Substances 0.000 claims description 4
- 229910000039 hydrogen halide Inorganic materials 0.000 claims description 4
- 239000007858 starting material Substances 0.000 claims description 4
- 230000017105 transposition Effects 0.000 claims description 4
- DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 125000001153 fluoro group Chemical group F* 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 238000006136 alcoholysis reaction Methods 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims 3
- 238000010438 heat treatment Methods 0.000 claims 3
- 150000007513 acids Chemical class 0.000 claims 2
- VEMKTZHHVJILDY-UXHICEINSA-N bioresmethrin Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)OCC1=COC(CC=2C=CC=CC=2)=C1 VEMKTZHHVJILDY-UXHICEINSA-N 0.000 claims 2
- 125000001246 bromo group Chemical group Br* 0.000 claims 2
- 239000003495 polar organic solvent Substances 0.000 claims 2
- 125000003158 alcohol group Chemical group 0.000 claims 1
- 125000002843 carboxylic acid group Chemical group 0.000 claims 1
- 230000000749 insecticidal effect Effects 0.000 claims 1
- 239000002917 insecticide Substances 0.000 claims 1
- 238000012423 maintenance Methods 0.000 claims 1
- 239000003880 polar aprotic solvent Substances 0.000 claims 1
- 239000002728 pyrethroid Substances 0.000 claims 1
- 230000006340 racemization Effects 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 11
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- 239000002585 base Substances 0.000 description 9
- 238000010992 reflux Methods 0.000 description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 230000004048 modification Effects 0.000 description 4
- 238000012986 modification Methods 0.000 description 4
- 239000001632 sodium acetate Substances 0.000 description 4
- 235000017281 sodium acetate Nutrition 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- -1 alkane carboxylic acids Chemical class 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- 229940126062 Compound A Drugs 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 229910000366 copper(II) sulfate Inorganic materials 0.000 description 2
- 125000004093 cyano group Chemical group *C#N 0.000 description 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 2
- 150000002825 nitriles Chemical class 0.000 description 2
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- 125000000453 2,2,2-trichloroethyl group Chemical group [H]C([H])(*)C(Cl)(Cl)Cl 0.000 description 1
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 1
- HFUWHULRJBGIQJ-UHFFFAOYSA-N 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carbonitrile Chemical compound CC1(C)C(C=C(Cl)Cl)C1C#N HFUWHULRJBGIQJ-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 229910001515 alkali metal fluoride Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 150000007514 bases Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 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
- 239000011737 fluorine Substances 0.000 description 1
- 238000001030 gas--liquid chromatography Methods 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- 239000011698 potassium fluoride Substances 0.000 description 1
- 235000003270 potassium fluoride Nutrition 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/45—Carboxylic acid nitriles having cyano groups bound to carbon atoms of rings other than six-membered aromatic rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8124110 | 1981-08-06 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH653012A5 true CH653012A5 (de) | 1985-12-13 |
Family
ID=10523751
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH4727/82A CH653012A5 (de) | 1981-08-06 | 1982-08-05 | Verfahren zur stereospezifischen herstellung von 1-cyano-2(2,2-dihalogenvinyl)-3,3-dimethylcyclopropan. |
Country Status (11)
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4000180A (en) * | 1974-08-14 | 1976-12-28 | Imperial Chemical Industries Limited | Process for preparing 2-dihalovinyl-3,3-dimethyl cyclo propane derivatives |
| GB1580203A (en) * | 1976-06-22 | 1980-11-26 | Shell Int Research | Preparation of cyclopropane derivatives |
| NZ185635A (en) * | 1976-11-18 | 1980-04-28 | Ici Ltd | Preparation of 3-dihalovinyl-2,2-dimethylcyclopropane carboxylic acid derivatives |
-
1982
- 1982-07-27 NL NL8203002A patent/NL8203002A/nl not_active Application Discontinuation
- 1982-07-28 CA CA000408291A patent/CA1181092A/en not_active Expired
- 1982-08-05 JP JP57135814A patent/JPS5829756A/ja active Granted
- 1982-08-05 GB GB08222631A patent/GB2104518B/en not_active Expired
- 1982-08-05 IT IT22753/82A patent/IT1152485B/it active
- 1982-08-05 DK DK351882A patent/DK158304C/da not_active IP Right Cessation
- 1982-08-05 CH CH4727/82A patent/CH653012A5/de not_active IP Right Cessation
- 1982-08-05 DE DE19823229311 patent/DE3229311A1/de active Granted
- 1982-08-05 BR BR8204605A patent/BR8204605A/pt not_active IP Right Cessation
- 1982-08-05 FR FR8213677A patent/FR2510993A1/fr active Granted
- 1982-08-05 BE BE0/208754A patent/BE894035A/nl not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5829756A (ja) | 1983-02-22 |
| BR8204605A (pt) | 1983-07-26 |
| BE894035A (nl) | 1983-02-07 |
| FR2510993A1 (fr) | 1983-02-11 |
| IT1152485B (it) | 1986-12-31 |
| JPH0323539B2 (enrdf_load_stackoverflow) | 1991-03-29 |
| FR2510993B1 (enrdf_load_stackoverflow) | 1984-12-14 |
| DE3229311C2 (enrdf_load_stackoverflow) | 1990-12-20 |
| GB2104518B (en) | 1985-09-18 |
| DK158304C (da) | 1990-10-01 |
| NL8203002A (nl) | 1983-03-01 |
| DE3229311A1 (de) | 1983-02-24 |
| IT8222753A0 (it) | 1982-08-05 |
| CA1181092A (en) | 1985-01-15 |
| DK158304B (da) | 1990-04-30 |
| DK351882A (da) | 1983-02-07 |
| GB2104518A (en) | 1983-03-09 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2536145A1 (de) | Verfahren zur herstellung von cyclopropanderivaten | |
| DE2751610A1 (de) | Verfahren zur herstellung von cyclopropanderivaten | |
| DE2730755C2 (de) | Verfahren zur Herstellung von Cyclopropanderivaten | |
| DE2437882A1 (de) | Verfahren zur herstellung von estern des 3-phenoxybenzylalkohols | |
| DE3854299T2 (de) | Umwandlung von pyrethroid-isomeren in aktivere formen. | |
| DE3229311C2 (enrdf_load_stackoverflow) | ||
| CH627155A5 (enrdf_load_stackoverflow) | ||
| DE68920073T2 (de) | Verfahren zur Verringerung der Racemisierung auf ein Mindestmass bei der Herstellung von optisch aktiven [(Aryloxy)phenoxy]propionat-Herbiziden. | |
| EP0012722B1 (de) | Verfahren zur Herstellung von optisch aktiven, in 3-Stellung substituierten 2-(2',2'-Dihalogenvinyl)-cyclopropan-1-carbonsäuren und deren Derivaten; 4-(2',2',2'-Trihalogenäthyl)-cyclobutan-1-sulfonsäuresalze und deren Herstellung | |
| CH626330A5 (en) | Process for preparing benzoyl cyanide | |
| DE3120969C2 (enrdf_load_stackoverflow) | ||
| EP0024588B1 (de) | Verfahren zur Herstellung von substituierten Cyclopropyl-carbonsäure-(alpha-cyano-3-phenoxy-benzyl)-estern | |
| DE2716771A1 (de) | Verfahren zur herstellung von estern von m-phenoxybenzylalkohol und seiner alpha-cyano- und alpha-aethinylderivate mit carbonsaeuren | |
| DE2614241A1 (de) | Verfahren zur herstellung von acylcyaniden | |
| DE2831555C2 (enrdf_load_stackoverflow) | ||
| EP0157225B1 (de) | Verfahren zur Herstellung von Benzimidazolyl,-Benzoxazolyl- und Benzthiazolyloxyphenoxypropionsäurederivaten | |
| DE69213761T2 (de) | Isomerisierungsverfahren | |
| DE1232127B (de) | Verfahren zur Herstellung von gesaettigten aliphatischen oder aromatischen Nitrilen | |
| DE2636384C2 (de) | Verfahren zur Herstellung von N,N-Diethyl-2-(α-naphthoxy)-propionamid | |
| DE2727613A1 (de) | Cyanosubstituierte cyclopropanderivate und verfahren zu ihrer herstellung | |
| DE2240663C3 (de) | Verfahren zur Herstellung von a -Chloraciylsäure | |
| DE2153356A1 (de) | Verfahren zur Herstellung von alpha Amlinocarbonsauren und ihren Derivaten | |
| DE935362C (de) | Verfahren zur Herstellung von Pentaerythrittetrachlorid | |
| EP0293752A2 (de) | Verfahren zur Herstellung von E-2-Propyl-2-pentensäure und physiologisch verträglichen Salzen derselben | |
| CH630593A5 (de) | Verfahren zur herstellung von 4-brom-2-chlorphenol. |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |