DE2630633C2 - - Google Patents
Info
- Publication number
- DE2630633C2 DE2630633C2 DE2630633A DE2630633A DE2630633C2 DE 2630633 C2 DE2630633 C2 DE 2630633C2 DE 2630633 A DE2630633 A DE 2630633A DE 2630633 A DE2630633 A DE 2630633A DE 2630633 C2 DE2630633 C2 DE 2630633C2
- Authority
- DE
- Germany
- Prior art keywords
- cyanide
- formula
- compound
- chlorobenzyl
- chloride
- 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
- IVYMIRMKXZAHRV-UHFFFAOYSA-N 4-chlorophenylacetonitrile Chemical compound ClC1=CC=C(CC#N)C=C1 IVYMIRMKXZAHRV-UHFFFAOYSA-N 0.000 claims description 17
- ULYZAYCEDJDHCC-UHFFFAOYSA-N isopropyl chloride Chemical compound CC(C)Cl ULYZAYCEDJDHCC-UHFFFAOYSA-N 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 14
- RBGSZIRWNWQDOK-UHFFFAOYSA-N 2-(4-chlorophenyl)-3-methylbutanenitrile Chemical compound CC(C)C(C#N)C1=CC=C(Cl)C=C1 RBGSZIRWNWQDOK-UHFFFAOYSA-N 0.000 claims description 11
- -1 4-chlorobenzyl halide Chemical class 0.000 claims description 11
- 150000003856 quaternary ammonium compounds Chemical class 0.000 claims description 11
- 238000006243 chemical reaction Methods 0.000 claims description 10
- 150000001875 compounds Chemical class 0.000 claims description 6
- 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 6
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 5
- 229910052783 alkali metal Inorganic materials 0.000 claims description 4
- 230000029936 alkylation Effects 0.000 claims description 3
- 238000005804 alkylation reaction Methods 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 238000009472 formulation Methods 0.000 claims 1
- 238000002955 isolation Methods 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical group [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 14
- 239000000203 mixture Substances 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- NHGXDBSUJJNIRV-UHFFFAOYSA-M tetrabutylammonium chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CCCC NHGXDBSUJJNIRV-UHFFFAOYSA-M 0.000 description 5
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 4
- JQZAEUFPPSRDOP-UHFFFAOYSA-N 1-chloro-4-(chloromethyl)benzene Chemical compound ClCC1=CC=C(Cl)C=C1 JQZAEUFPPSRDOP-UHFFFAOYSA-N 0.000 description 3
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- VTJMSIIXXKNIDJ-UHFFFAOYSA-N 2-(4-chlorophenyl)-3-methylbutyric acid Chemical compound CC(C)C(C(O)=O)C1=CC=C(Cl)C=C1 VTJMSIIXXKNIDJ-UHFFFAOYSA-N 0.000 description 2
- NPDACUSDTOMAMK-UHFFFAOYSA-N 4-Chlorotoluene Chemical compound CC1=CC=C(Cl)C=C1 NPDACUSDTOMAMK-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 150000007962 benzene acetonitriles Chemical class 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- QEVYQHFZTXUKJU-UHFFFAOYSA-M methyl-tri(octan-2-yl)azanium;chloride Chemical compound [Cl-].CCCCCCC(C)[N+](C)(C(C)CCCCCC)C(C)CCCCCC QEVYQHFZTXUKJU-UHFFFAOYSA-M 0.000 description 2
- SUSQOBVLVYHIEX-UHFFFAOYSA-N o-phenylene-diaceto-nitrile Natural products N#CCC1=CC=CC=C1 SUSQOBVLVYHIEX-UHFFFAOYSA-N 0.000 description 2
- NAMYKGVDVNBCFQ-UHFFFAOYSA-N 2-bromopropane Chemical compound CC(C)Br NAMYKGVDVNBCFQ-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 239000002168 alkylating agent Substances 0.000 description 1
- 229940100198 alkylating agent Drugs 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- KQNZLOUWXSAZGD-UHFFFAOYSA-N benzylperoxymethylbenzene Chemical compound C=1C=CC=CC=1COOCC1=CC=CC=C1 KQNZLOUWXSAZGD-UHFFFAOYSA-N 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000013065 commercial product Substances 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 230000000749 insecticidal effect Effects 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 150000005376 secondary alkyl halides Chemical class 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
- 238000001228 spectrum Methods 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
- C07C255/32—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring
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 (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2890075 | 1975-07-09 | ||
| GB2886975A GB1528043A (en) | 1975-07-09 | 1975-07-09 | Process for the preparation of nitrile derivatives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2630633A1 DE2630633A1 (de) | 1977-01-27 |
| DE2630633C2 true DE2630633C2 (en, 2012) | 1988-05-26 |
Family
ID=26259605
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19762630633 Granted DE2630633A1 (de) | 1975-07-09 | 1976-07-07 | Verfahren zur herstellung substituierter benzylnitrilderivate |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US4056509A (en, 2012) |
| JP (1) | JPS5933584B2 (en, 2012) |
| AU (1) | AU500150B2 (en, 2012) |
| BR (1) | BR7604436A (en, 2012) |
| CH (1) | CH619447A5 (en, 2012) |
| DD (1) | DD125678A5 (en, 2012) |
| DE (1) | DE2630633A1 (en, 2012) |
| FR (1) | FR2317281A1 (en, 2012) |
| HU (1) | HU174381B (en, 2012) |
| IL (1) | IL49985A (en, 2012) |
| IT (1) | IT1062521B (en, 2012) |
| NL (1) | NL187392C (en, 2012) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH601197A5 (en, 2012) * | 1976-09-29 | 1978-06-30 | Ciba Geigy Ag | |
| GB1591214A (en) * | 1977-05-23 | 1981-06-17 | Sumitomo Chemical Co | Recovery of a tertiary amine or quaternary ammonium catalyst used in the production of a-substituted benzyl nitriles |
| HU175219B (hu) * | 1977-10-20 | 1980-06-28 | Chinoin Gyogyszer Es Vegyeszet | Sposob poluchenija slozhnykh benzil'nykh ehfirov s pomoshch'ju nukleofil'noj reakcii zameshchenija katalizirovannoj vodoj v geterogennoj faze |
| US4144265A (en) * | 1978-07-17 | 1979-03-13 | The Dow Chemical Company | Process for the manufacture of m-trifluoromethyl benzyl nitrile |
| JPS5559157A (en) * | 1978-10-30 | 1980-05-02 | Ihara Chem Ind Co Ltd | Production alpha-isopropyl-halo substituted phenylacetonitrile |
| US4186270A (en) * | 1978-12-26 | 1980-01-29 | The Dow Chemical Company | Process for making 2-(4-isobutylphenyl)propionic acid and related compounds |
| US4242274A (en) * | 1979-06-18 | 1980-12-30 | Mallinckrodt, Inc. | Process for the preparation of 2,2-diphenyl-4-(dimethylamino)-pentane nitrile |
| US4699991A (en) * | 1981-11-23 | 1987-10-13 | Petrarch Systems Inc. | Methods of using silacrown ethers as catalysts |
| KR20220080100A (ko) * | 2019-10-11 | 2022-06-14 | 상뜨르 나쇼날 드 라 러쉐르쉬 샹띠피끄 | 세포를 항암제에 민감하게 만드는 새로운 카바졸 유도체 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2779781A (en) * | 1954-12-29 | 1957-01-29 | Du Pont | Cyanidation catalysts |
| US3413309A (en) * | 1963-02-18 | 1968-11-26 | Mieczyslaw J Makosza | Process for preparing nitriles of cycloaliphatic or heterocyclic acids |
| GB1227144A (en, 2012) | 1967-04-05 | 1971-04-07 | ||
| DE1668034A1 (de) * | 1967-10-21 | 1971-07-22 | Bayer Ag | Verfahren zur Herstellung von Benzylcyaniden und deren Homologen |
| HU164015B (en, 2012) * | 1971-05-31 | 1973-12-28 | ||
| JPS5163145A (en) * | 1974-11-26 | 1976-06-01 | Sumitomo Chemical Co | 33 mechiru 22 * 44 harogenofueniru * buchironitoriruno seizoho |
-
1976
- 1976-06-24 US US05/699,815 patent/US4056509A/en not_active Expired - Lifetime
- 1976-07-06 IL IL49985A patent/IL49985A/xx unknown
- 1976-07-07 DE DE19762630633 patent/DE2630633A1/de active Granted
- 1976-07-07 JP JP51080036A patent/JPS5933584B2/ja not_active Expired
- 1976-07-07 CH CH871376A patent/CH619447A5/de not_active IP Right Cessation
- 1976-07-07 DD DD193744A patent/DD125678A5/xx unknown
- 1976-07-07 BR BR4436/76A patent/BR7604436A/pt unknown
- 1976-07-07 IT IT25100/76A patent/IT1062521B/it active
- 1976-07-07 NL NLAANVRAGE7607483,A patent/NL187392C/xx not_active IP Right Cessation
- 1976-07-07 FR FR7620734A patent/FR2317281A1/fr active Granted
- 1976-07-08 HU HU76SE1840A patent/HU174381B/hu unknown
- 1976-07-09 AU AU15776/76A patent/AU500150B2/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| IL49985A (en) | 1978-10-31 |
| HU174381B (hu) | 1979-12-28 |
| NL187392B (nl) | 1991-04-16 |
| BR7604436A (pt) | 1978-01-31 |
| FR2317281A1 (fr) | 1977-02-04 |
| DD125678A5 (en, 2012) | 1977-05-11 |
| JPS5933584B2 (ja) | 1984-08-16 |
| CH619447A5 (en, 2012) | 1980-09-30 |
| IT1062521B (it) | 1984-10-20 |
| IL49985A0 (en) | 1976-09-30 |
| AU1577676A (en) | 1978-01-12 |
| DE2630633A1 (de) | 1977-01-27 |
| FR2317281B1 (en, 2012) | 1979-04-06 |
| NL7607483A (nl) | 1977-01-11 |
| US4056509A (en) | 1977-11-01 |
| JPS5210234A (en) | 1977-01-26 |
| AU500150B2 (en) | 1979-05-10 |
| NL187392C (nl) | 1991-09-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |