CH628326A5 - Process for preparing cyano-substituted cyclopropane derivatives - Google Patents
Process for preparing cyano-substituted cyclopropane derivatives Download PDFInfo
- Publication number
- CH628326A5 CH628326A5 CH752577A CH752577A CH628326A5 CH 628326 A5 CH628326 A5 CH 628326A5 CH 752577 A CH752577 A CH 752577A CH 752577 A CH752577 A CH 752577A CH 628326 A5 CH628326 A5 CH 628326A5
- Authority
- CH
- Switzerland
- Prior art keywords
- formula
- ammonia
- heated
- dichlorovinyl
- cyclopropane
- Prior art date
Links
- -1 cyano-substituted cyclopropane Chemical class 0.000 title description 3
- 238000004519 manufacturing process Methods 0.000 title 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 18
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 16
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 claims description 10
- 229910021529 ammonia Inorganic materials 0.000 claims description 8
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 5
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 4
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methylaniline Chemical compound CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 claims description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 4
- 239000000010 aprotic solvent Substances 0.000 claims description 4
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims description 4
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- YMGUBTXCNDTFJI-UHFFFAOYSA-M cyclopropanecarboxylate Chemical compound [O-]C(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-M 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- BMVXCPBXGZKUPN-UHFFFAOYSA-N 1-hexanamine Chemical compound CCCCCCN BMVXCPBXGZKUPN-UHFFFAOYSA-N 0.000 claims description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 2
- 241000251730 Chondrichthyes Species 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
- YCSKLPVYSJOCMO-UHFFFAOYSA-N 1-cyano-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate;dimethyl(phenyl)azanium Chemical compound C[NH+](C)C1=CC=CC=C1.CC1(C)C(C=C(Cl)Cl)C1(C#N)C([O-])=O YCSKLPVYSJOCMO-UHFFFAOYSA-N 0.000 description 1
- 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
- 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
- 101001072501 Sarocladium strictum Glucooligosaccharide oxidase Proteins 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- AFRPUUYIQUBHLH-UHFFFAOYSA-N azane;cyclopropanecarboxylic acid Chemical class [NH4+].[O-]C(=O)C1CC1 AFRPUUYIQUBHLH-UHFFFAOYSA-N 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical class OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 description 1
- 150000001942 cyclopropanes Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000001030 gas--liquid chromatography Methods 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 239000003880 polar aprotic solvent Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 238000010183 spectrum analysis Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 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
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2589576A GB1580202A (en) | 1976-06-22 | 1976-06-22 | Process for the preparation of cyclopropanecarbonitriles |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH628326A5 true CH628326A5 (en) | 1982-02-26 |
Family
ID=10235106
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH752577A CH628326A5 (en) | 1976-06-22 | 1977-06-20 | Process for preparing cyano-substituted cyclopropane derivatives |
Country Status (11)
| Country | Link |
|---|---|
| JP (1) | JPS52156838A (cs) |
| BE (1) | BE855693A (cs) |
| BR (1) | BR7703996A (cs) |
| CA (1) | CA1085873A (cs) |
| CH (1) | CH628326A5 (cs) |
| DE (1) | DE2727612C2 (cs) |
| DK (1) | DK155829C (cs) |
| FR (1) | FR2355810A1 (cs) |
| GB (1) | GB1580202A (cs) |
| IT (1) | IT1080224B (cs) |
| NL (1) | NL188639C (cs) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2606635A1 (de) * | 1976-02-19 | 1977-08-25 | Bayer Ag | Verfahren zur herstellung von 2,2-dimethyl-3-(2',2'-dichlorvinyl) -cyclopropan-1-carbonsaeure |
-
1976
- 1976-06-22 GB GB2589576A patent/GB1580202A/en not_active Expired
-
1977
- 1977-06-03 CA CA279,843A patent/CA1085873A/en not_active Expired
- 1977-06-15 BE BE1008192A patent/BE855693A/xx not_active IP Right Cessation
- 1977-06-20 FR FR7718842A patent/FR2355810A1/fr active Granted
- 1977-06-20 DK DK271777A patent/DK155829C/da not_active IP Right Cessation
- 1977-06-20 IT IT2486777A patent/IT1080224B/it active
- 1977-06-20 JP JP7226077A patent/JPS52156838A/ja active Pending
- 1977-06-20 DE DE19772727612 patent/DE2727612C2/de not_active Expired
- 1977-06-20 NL NL7706754A patent/NL188639C/xx not_active IP Right Cessation
- 1977-06-20 BR BR7703996A patent/BR7703996A/pt unknown
- 1977-06-20 CH CH752577A patent/CH628326A5/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| DE2727612C2 (de) | 1986-03-06 |
| CA1085873A (en) | 1980-09-16 |
| NL188639B (nl) | 1992-03-16 |
| DK155829C (da) | 1989-10-02 |
| BR7703996A (pt) | 1978-04-25 |
| GB1580202A (en) | 1980-11-26 |
| IT1080224B (it) | 1985-05-16 |
| DK271777A (da) | 1977-12-23 |
| FR2355810B1 (cs) | 1978-10-20 |
| NL188639C (nl) | 1992-08-17 |
| BE855693A (nl) | 1977-12-15 |
| FR2355810A1 (fr) | 1978-01-20 |
| JPS52156838A (en) | 1977-12-27 |
| DK155829B (da) | 1989-05-22 |
| NL7706754A (nl) | 1977-12-27 |
| DE2727612A1 (de) | 1978-01-05 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |