CA1123006A - Preparation of cyclopropane derivatives - Google Patents
Preparation of cyclopropane derivativesInfo
- Publication number
- CA1123006A CA1123006A CA277,560A CA277560A CA1123006A CA 1123006 A CA1123006 A CA 1123006A CA 277560 A CA277560 A CA 277560A CA 1123006 A CA1123006 A CA 1123006A
- Authority
- CA
- Canada
- Prior art keywords
- process according
- carried out
- general formula
- chlorine
- alkyl group
- 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
- 238000002360 preparation method Methods 0.000 title claims abstract description 7
- 125000001559 cyclopropyl group Chemical class [H]C1([H])C([H])([H])C1([H])* 0.000 title abstract 2
- 238000000034 method Methods 0.000 claims abstract description 17
- 150000001875 compounds Chemical class 0.000 claims abstract description 14
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 8
- 239000000460 chlorine Substances 0.000 claims abstract description 8
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 8
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 7
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims abstract description 7
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims abstract description 4
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 4
- 239000011737 fluorine Substances 0.000 claims abstract description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 4
- 230000000911 decarboxylating effect Effects 0.000 claims abstract description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 14
- 239000002585 base Substances 0.000 claims description 11
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical group CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 10
- -1 cyano-substituted cyclopropane Chemical class 0.000 claims description 9
- 229910052783 alkali metal Inorganic materials 0.000 claims description 7
- 229910021529 ammonia Inorganic materials 0.000 claims description 7
- 238000006243 chemical reaction Methods 0.000 claims description 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 6
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 claims description 4
- 150000001340 alkali metals Chemical group 0.000 claims description 4
- 229910052784 alkaline earth metal Chemical group 0.000 claims description 4
- 239000001632 sodium acetate Substances 0.000 claims description 4
- 235000017281 sodium acetate Nutrition 0.000 claims description 4
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 claims description 3
- 150000001342 alkaline earth metals Chemical group 0.000 claims description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 239000003125 aqueous solvent Substances 0.000 claims 4
- 125000001453 quaternary ammonium group Chemical group 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 239000002253 acid Substances 0.000 description 9
- 239000000543 intermediate Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 238000006114 decarboxylation reaction Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 150000001942 cyclopropanes Chemical class 0.000 description 2
- 125000003963 dichloro group Chemical group Cl* 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 2
- 238000007363 ring formation reaction Methods 0.000 description 2
- IOVGROKTTNBUGK-SJCJKPOMSA-N ritodrine Chemical compound N([C@@H](C)[C@H](O)C=1C=CC(O)=CC=1)CCC1=CC=C(O)C=C1 IOVGROKTTNBUGK-SJCJKPOMSA-N 0.000 description 2
- QUBRLGZRCKCFDY-UHFFFAOYSA-N 1-cyano-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylic acid Chemical compound CC1(C)C(C=C(Cl)Cl)C1(C#N)C(O)=O QUBRLGZRCKCFDY-UHFFFAOYSA-N 0.000 description 1
- PXOSYYJPWXXRJX-UHFFFAOYSA-N 6,6,6-trichlorohexanoic acid Chemical compound OC(=O)CCCCC(Cl)(Cl)Cl PXOSYYJPWXXRJX-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 229940126062 Compound A Drugs 0.000 description 1
- LVZWSLJZHVFIQJ-UHFFFAOYSA-N Cyclopropane Chemical compound C1CC1 LVZWSLJZHVFIQJ-UHFFFAOYSA-N 0.000 description 1
- 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 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 241001072332 Monia Species 0.000 description 1
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 1
- 230000009102 absorption Effects 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical compound OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 description 1
- 238000006704 dehydrohalogenation reaction Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- QWXYZCJEXYQNEI-OSZHWHEXSA-N intermediate I Chemical compound COC(=O)[C@@]1(C=O)[C@H]2CC=[N+](C\C2=C\C)CCc2c1[nH]c1ccccc21 QWXYZCJEXYQNEI-OSZHWHEXSA-N 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- MOJJWIKVYFQNSC-UHFFFAOYSA-N methyl 4,6,6,6-tetrachloro-2-cyano-3,3-dimethylhexanoate Chemical compound COC(=O)C(C#N)C(C)(C)C(Cl)CC(Cl)(Cl)Cl MOJJWIKVYFQNSC-UHFFFAOYSA-N 0.000 description 1
- KERBAAIBDHEFDD-UHFFFAOYSA-N n-ethylformamide Chemical compound CCNC=O KERBAAIBDHEFDD-UHFFFAOYSA-N 0.000 description 1
- 239000003880 polar aprotic solvent Substances 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000002728 pyrethroid Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB25896/76 | 1976-06-22 | ||
| GB2589676A GB1580203A (en) | 1976-06-22 | 1976-06-22 | Preparation of cyclopropane derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1123006A true CA1123006A (en) | 1982-05-04 |
Family
ID=10235120
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA277,560A Expired CA1123006A (en) | 1976-06-22 | 1977-05-03 | Preparation of cyclopropane derivatives |
Country Status (11)
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK276879A (da) * | 1978-07-18 | 1980-01-19 | Ici Ltd | Fremgangsmaade til fremstilling af cyclopropannitriler |
| FR2485004A1 (fr) * | 1980-06-20 | 1981-12-24 | Roussel Uclaf | Derives cyclopropane-1-carboxyliques et leurs sels, leur preparation et leur application a la synthese d'intermediaires de composes pyrethrinoides de configuration cis |
| EP0064781B1 (en) * | 1981-04-30 | 1984-05-23 | Shell Internationale Researchmaatschappij B.V. | Process for the preparation of cyclopropane compounds |
| NL8203002A (nl) * | 1981-08-06 | 1983-03-01 | Shell Int Research | Stereospecifieke decarboxylering van dihalogeenvinylcyclopropaancarbonzuren. |
| GB2127012A (en) * | 1982-09-22 | 1984-04-04 | Shell Int Research | Process for the preparation of cyclopropane compounds |
-
1976
- 1976-06-22 GB GB2589676A patent/GB1580203A/en not_active Expired
-
1977
- 1977-05-03 CA CA277,560A patent/CA1123006A/en not_active Expired
- 1977-06-15 BE BE1008190A patent/BE855691A/xx not_active IP Right Cessation
- 1977-06-20 DK DK271877A patent/DK156955C/da not_active IP Right Cessation
- 1977-06-20 DE DE19772727613 patent/DE2727613A1/de active Granted
- 1977-06-20 JP JP7226277A patent/JPS52156839A/ja active Granted
- 1977-06-20 BR BR7703975A patent/BR7703975A/pt unknown
- 1977-06-20 FR FR7718843A patent/FR2355811A1/fr active Granted
- 1977-06-20 NL NL7706755A patent/NL7706755A/xx not_active Application Discontinuation
- 1977-06-20 CH CH752677A patent/CH629758A5/de not_active IP Right Cessation
- 1977-06-20 IT IT2486677A patent/IT1080226B/it active
-
1986
- 1986-03-24 JP JP61064300A patent/JPS61233658A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS61233658A (ja) | 1986-10-17 |
| BE855691A (nl) | 1977-12-15 |
| JPS638100B2 (enrdf_load_stackoverflow) | 1988-02-19 |
| JPS6140660B2 (enrdf_load_stackoverflow) | 1986-09-10 |
| DK271877A (da) | 1977-12-23 |
| FR2355811A1 (fr) | 1978-01-20 |
| GB1580203A (en) | 1980-11-26 |
| DK156955C (da) | 1990-02-26 |
| DE2727613A1 (de) | 1977-12-29 |
| BR7703975A (pt) | 1978-04-25 |
| DK156955B (da) | 1989-10-23 |
| FR2355811B1 (enrdf_load_stackoverflow) | 1980-12-05 |
| IT1080226B (it) | 1985-05-16 |
| NL7706755A (nl) | 1977-12-27 |
| CH629758A5 (en) | 1982-05-14 |
| DE2727613C2 (enrdf_load_stackoverflow) | 1988-03-03 |
| JPS52156839A (en) | 1977-12-27 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |