CA1121831A - Preparation of cyclopropane derivatives - Google Patents
Preparation of cyclopropane derivativesInfo
- Publication number
- CA1121831A CA1121831A CA000294304A CA294304A CA1121831A CA 1121831 A CA1121831 A CA 1121831A CA 000294304 A CA000294304 A CA 000294304A CA 294304 A CA294304 A CA 294304A CA 1121831 A CA1121831 A CA 1121831A
- Authority
- CA
- Canada
- Prior art keywords
- acid
- ester
- zinc
- alkyl
- carbon atoms
- 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 6
- 125000001559 cyclopropyl group Chemical class [H]C1([H])C([H])([H])C1([H])* 0.000 title 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims abstract description 38
- 239000011701 zinc Substances 0.000 claims abstract description 30
- 229910052725 zinc Inorganic materials 0.000 claims abstract description 30
- 239000002253 acid Substances 0.000 claims abstract description 24
- 150000001875 compounds Chemical class 0.000 claims abstract description 17
- 150000002148 esters Chemical class 0.000 claims abstract description 15
- 238000000034 method Methods 0.000 claims abstract description 15
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 12
- 125000005843 halogen group Chemical group 0.000 claims abstract description 11
- 150000003839 salts Chemical class 0.000 claims abstract description 10
- 150000008064 anhydrides Chemical class 0.000 claims abstract description 9
- 229910052740 iodine Inorganic materials 0.000 claims abstract description 8
- 125000005907 alkyl ester group Chemical group 0.000 claims abstract description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 6
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 6
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 4
- YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical compound OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 claims abstract description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 51
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 14
- 150000003863 ammonium salts Chemical class 0.000 claims description 9
- 150000003857 carboxamides Chemical class 0.000 claims description 8
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 8
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 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 claims description 5
- 239000000460 chlorine Substances 0.000 claims description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- 238000005695 dehalogenation reaction Methods 0.000 claims description 3
- 229910052783 alkali metal Inorganic materials 0.000 claims 2
- 150000001340 alkali metals Chemical class 0.000 claims 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims 2
- 150000001342 alkaline earth metals Chemical class 0.000 claims 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- 235000019260 propionic acid Nutrition 0.000 claims 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims 1
- 125000003917 carbamoyl group Chemical class [H]N([H])C(*)=O 0.000 abstract 2
- 239000002917 insecticide Substances 0.000 abstract 1
- 239000002728 pyrethroid Substances 0.000 abstract 1
- 230000002194 synthesizing effect Effects 0.000 abstract 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 18
- 235000011054 acetic acid Nutrition 0.000 description 15
- 229960000583 acetic acid Drugs 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- YUBCVMNXGPVXID-UHFFFAOYSA-N 2,2-dichloro-3,3-dimethylcyclopropane-1-carboxylic acid Chemical compound CC1(C)C(C(O)=O)C1(Cl)Cl YUBCVMNXGPVXID-UHFFFAOYSA-N 0.000 description 9
- 235000019270 ammonium chloride Nutrition 0.000 description 9
- 238000010992 reflux Methods 0.000 description 8
- 239000007788 liquid Substances 0.000 description 7
- 238000003756 stirring Methods 0.000 description 6
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 150000001942 cyclopropanes Chemical class 0.000 description 4
- 238000006298 dechlorination reaction Methods 0.000 description 4
- -1 hydrocarbyl tin hydride Chemical compound 0.000 description 4
- 230000035484 reaction time Effects 0.000 description 4
- GHXJAGHRKSJMPQ-UHFFFAOYSA-N 3-chloro-2,2-dimethylcyclopropane-1-carboxylic acid Chemical compound CC1(C)C(Cl)C1C(O)=O GHXJAGHRKSJMPQ-UHFFFAOYSA-N 0.000 description 3
- 230000009102 absorption Effects 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 238000010908 decantation Methods 0.000 description 3
- ZJAJKMDQAODLNY-UHFFFAOYSA-N methyl 2,2-dichloro-3,3-dimethylcyclopropane-1-carboxylate Chemical compound COC(=O)C1C(C)(C)C1(Cl)Cl ZJAJKMDQAODLNY-UHFFFAOYSA-N 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 3
- VKHSRYYWICBVOW-UHFFFAOYSA-N 2-chloro-1,1-dimethylcyclopropane Chemical compound CC1(C)CC1Cl VKHSRYYWICBVOW-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- 150000004702 methyl esters Chemical class 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- QCRGTFXKYABKHU-UHFFFAOYSA-N tert-butyl 3-chloro-2,2-dimethylcyclopropane-1-carboxylate Chemical compound ClC1C(C1C(=O)OC(C)(C)C)(C)C QCRGTFXKYABKHU-UHFFFAOYSA-N 0.000 description 2
- 229910000083 tin tetrahydride Inorganic materials 0.000 description 2
- DBGVGMSCBYYSLD-UHFFFAOYSA-N tributylstannane Chemical compound CCCC[SnH](CCCC)CCCC DBGVGMSCBYYSLD-UHFFFAOYSA-N 0.000 description 2
- LFKAUQAAELSUAM-UHFFFAOYSA-N 3-tert-butyl-1,1-dichloro-2,2-dimethylcyclopropane Chemical compound CC(C)(C)C1C(C)(C)C1(Cl)Cl LFKAUQAAELSUAM-UHFFFAOYSA-N 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- 101100353161 Drosophila melanogaster prel gene Proteins 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 101100536883 Legionella pneumophila subsp. pneumophila (strain Philadelphia 1 / ATCC 33152 / DSM 7513) thi5 gene Proteins 0.000 description 1
- 101100240664 Schizosaccharomyces pombe (strain 972 / ATCC 24843) nmt1 gene Proteins 0.000 description 1
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 1
- 150000001266 acyl halides Chemical class 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 1
- 239000001166 ammonium sulphate Substances 0.000 description 1
- 235000011130 ammonium sulphate Nutrition 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 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 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- YMGUBTXCNDTFJI-UHFFFAOYSA-M cyclopropanecarboxylate Chemical compound [O-]C(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-M 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000001183 hydrocarbyl group Chemical group 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- VPQWGHHXCIHSCW-UHFFFAOYSA-N methyl 3-chloro-2,2-dimethylcyclopropane-1-carboxylate Chemical compound COC(=O)C1C(Cl)C1(C)C VPQWGHHXCIHSCW-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910052756 noble gas Inorganic materials 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- KXCAEQNNTZANTK-UHFFFAOYSA-N stannane Chemical compound [SnH4] KXCAEQNNTZANTK-UHFFFAOYSA-N 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- LNEFGAYKTMMXDW-UHFFFAOYSA-N tert-butyl 2,2-dichloro-3,3-dimethylcyclopropane-1-carboxylate Chemical compound CC(C)(C)OC(=O)C1C(C)(C)C1(Cl)Cl LNEFGAYKTMMXDW-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3164/77 | 1977-01-26 | ||
| GB3164/77A GB1594224A (en) | 1977-01-26 | 1977-01-26 | Preparation of cyclopropane derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1121831A true CA1121831A (en) | 1982-04-13 |
Family
ID=9753142
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000294304A Expired CA1121831A (en) | 1977-01-26 | 1978-01-04 | Preparation of cyclopropane derivatives |
Country Status (11)
| Country | Link |
|---|---|
| JP (1) | JPS5392743A (en, 2012) |
| BE (1) | BE863272A (en, 2012) |
| BR (1) | BR7800411A (en, 2012) |
| CA (1) | CA1121831A (en, 2012) |
| CH (1) | CH634035A5 (en, 2012) |
| DE (1) | DE2802967A1 (en, 2012) |
| FR (1) | FR2378740A1 (en, 2012) |
| GB (1) | GB1594224A (en, 2012) |
| IT (1) | IT7819574A0 (en, 2012) |
| MX (1) | MX4672E (en, 2012) |
| NL (1) | NL7800811A (en, 2012) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3026093C2 (de) * | 1980-07-10 | 1983-02-10 | Degussa Ag, 6000 Frankfurt | 1-Methyl-2-chlorcyclopropancarbonsäure und deren verzweigte und unverzweigte C↓1↓ bis C↓6↓-Alkylester, sowie Verfahren zu deren Herstellung |
| CN1304356C (zh) * | 2003-01-07 | 2007-03-14 | 第一制药株式会社 | 还原脱卤方法 |
-
1977
- 1977-01-26 GB GB3164/77A patent/GB1594224A/en not_active Expired
-
1978
- 1978-01-04 CA CA000294304A patent/CA1121831A/en not_active Expired
- 1978-01-24 JP JP588578A patent/JPS5392743A/ja active Pending
- 1978-01-24 IT IT7819574A patent/IT7819574A0/it unknown
- 1978-01-24 MX MX678678U patent/MX4672E/es unknown
- 1978-01-24 BE BE184604A patent/BE863272A/xx not_active IP Right Cessation
- 1978-01-24 BR BR7800411A patent/BR7800411A/pt unknown
- 1978-01-24 DE DE19782802967 patent/DE2802967A1/de not_active Withdrawn
- 1978-01-24 FR FR7801895A patent/FR2378740A1/fr active Granted
- 1978-01-24 CH CH75178A patent/CH634035A5/de not_active IP Right Cessation
- 1978-01-24 NL NL7800811A patent/NL7800811A/xx not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| CH634035A5 (en) | 1983-01-14 |
| MX4672E (es) | 1982-07-23 |
| DE2802967A1 (de) | 1978-07-27 |
| NL7800811A (nl) | 1978-07-28 |
| GB1594224A (en) | 1981-07-30 |
| IT7819574A0 (it) | 1978-01-24 |
| BE863272A (fr) | 1978-07-24 |
| BR7800411A (pt) | 1978-08-22 |
| JPS5392743A (en) | 1978-08-15 |
| FR2378740A1 (fr) | 1978-08-25 |
| FR2378740B1 (en, 2012) | 1981-08-21 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |