NO821817L - Fremgangsmaate for fremstilling av basisk substituert fenylacetonitriler. - Google Patents
Fremgangsmaate for fremstilling av basisk substituert fenylacetonitriler.Info
- Publication number
- NO821817L NO821817L NO821817A NO821817A NO821817L NO 821817 L NO821817 L NO 821817L NO 821817 A NO821817 A NO 821817A NO 821817 A NO821817 A NO 821817A NO 821817 L NO821817 L NO 821817L
- Authority
- NO
- Norway
- Prior art keywords
- formula
- carbon atoms
- reaction
- solid
- acetonitrils
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 16
- 238000002360 preparation method Methods 0.000 title description 2
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical class [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 title 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 18
- 238000006243 chemical reaction Methods 0.000 claims description 10
- 150000001875 compounds Chemical class 0.000 claims description 8
- SUSQOBVLVYHIEX-UHFFFAOYSA-N o-phenylene-diaceto-nitrile Natural products N#CCC1=CC=CC=C1 SUSQOBVLVYHIEX-UHFFFAOYSA-N 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 150000007962 benzene acetonitriles Chemical class 0.000 claims description 5
- 239000007791 liquid phase Substances 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 229910052740 iodine Inorganic materials 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 229910052700 potassium Inorganic materials 0.000 claims description 4
- -1 α-substituted phenylacetonitrile Chemical class 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- 125000001931 aliphatic group Chemical group 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 239000000460 chlorine Substances 0.000 claims description 3
- 125000004122 cyclic group Chemical group 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 229920006395 saturated elastomer Polymers 0.000 claims description 3
- 239000007790 solid phase Substances 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 239000003444 phase transfer catalyst Substances 0.000 claims description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- 239000003795 chemical substances by application Substances 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 4
- HJBBKVHYQQUPQW-UHFFFAOYSA-N 3-chloro-n-[2-(3,4-dimethoxyphenyl)ethyl]-n-methylpropan-1-amine Chemical compound COC1=CC=C(CCN(C)CCCCl)C=C1OC HJBBKVHYQQUPQW-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 125000002524 organometallic group Chemical group 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- DPKBAXPHAYBPRL-UHFFFAOYSA-M tetrabutylazanium;iodide Chemical compound [I-].CCCC[N+](CCCC)(CCCC)CCCC DPKBAXPHAYBPRL-UHFFFAOYSA-M 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- XEZNGIUYQVAUSS-UHFFFAOYSA-N 18-crown-6 Chemical compound C1COCCOCCOCCOCCOCCO1 XEZNGIUYQVAUSS-UHFFFAOYSA-N 0.000 description 1
- NFXAXMOAVPLEBH-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-3-methylbutanenitrile Chemical compound COC1=CC=C(C(C#N)C(C)C)C=C1OC NFXAXMOAVPLEBH-UHFFFAOYSA-N 0.000 description 1
- BATQRRPXKXQYAX-UHFFFAOYSA-N 3-methyl-2-(3,4,5-trimethoxyphenyl)butanenitrile Chemical compound COC1=CC(C(C#N)C(C)C)=CC(OC)=C1OC BATQRRPXKXQYAX-UHFFFAOYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 125000002619 bicyclic group Chemical group 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 150000003983 crown ethers Chemical class 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- YSSSPARMOAYJTE-UHFFFAOYSA-N dibenzo-18-crown-6 Chemical compound O1CCOCCOC2=CC=CC=C2OCCOCCOC2=CC=CC=C21 YSSSPARMOAYJTE-UHFFFAOYSA-N 0.000 description 1
- 230000000916 dilatatory effect Effects 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- SHFJWMWCIHQNCP-UHFFFAOYSA-M hydron;tetrabutylazanium;sulfate Chemical compound OS([O-])(=O)=O.CCCC[N+](CCCC)(CCCC)CCCC SHFJWMWCIHQNCP-UHFFFAOYSA-M 0.000 description 1
- 150000004694 iodide salts Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- MUBZPKHOEPUJKR-UHFFFAOYSA-M oxalate(1-) Chemical compound OC(=O)C([O-])=O MUBZPKHOEPUJKR-UHFFFAOYSA-M 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 125000005207 tetraalkylammonium group Chemical group 0.000 description 1
- RKHXQBLJXBGEKF-UHFFFAOYSA-M tetrabutylphosphanium;bromide Chemical compound [Br-].CCCC[P+](CCCC)(CCCC)CCCC RKHXQBLJXBGEKF-UHFFFAOYSA-M 0.000 description 1
- IBWGNZVCJVLSHB-UHFFFAOYSA-M tetrabutylphosphanium;chloride Chemical compound [Cl-].CCCC[P+](CCCC)(CCCC)CCCC IBWGNZVCJVLSHB-UHFFFAOYSA-M 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- 230000007306 turnover Effects 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/14—Preparation of carboxylic acid nitriles by reaction of cyanides with halogen-containing compounds with replacement of halogen atoms by cyano groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Toxicology (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 |
|---|---|---|---|
| DE19813121766 DE3121766A1 (de) | 1981-06-02 | 1981-06-02 | Verfahren zur herstellung basisch substituierter phenylacetonitrile |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO821817L true NO821817L (no) | 1982-12-03 |
Family
ID=6133687
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO821817A NO821817L (no) | 1981-06-02 | 1982-06-01 | Fremgangsmaate for fremstilling av basisk substituert fenylacetonitriler. |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US4418017A (fr) |
| EP (1) | EP0066246A3 (fr) |
| JP (1) | JPS57200348A (fr) |
| AU (1) | AU8436882A (fr) |
| CA (1) | CA1171430A (fr) |
| CS (1) | CS228932B2 (fr) |
| DE (1) | DE3121766A1 (fr) |
| DK (1) | DK245682A (fr) |
| FI (1) | FI821735A0 (fr) |
| IL (1) | IL65807A0 (fr) |
| NO (1) | NO821817L (fr) |
| YU (1) | YU114382A (fr) |
| ZA (1) | ZA823738B (fr) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3344755A1 (de) * | 1983-12-10 | 1985-06-20 | Basf Ag, 6700 Ludwigshafen | 1,7-diphenyl-3-methylaza-7-cyan-8-methyl-nonan zur verwendung bei der bekaempfung von krankheiten |
| US4612329A (en) * | 1984-10-17 | 1986-09-16 | Hokuriku Pharmaceutical Co., Ltd. | Pharmaceutical alpha-aminoalkyl-alpha-alkylphenylacetonitriles |
| US5247119A (en) * | 1990-12-12 | 1993-09-21 | G. D. Searle & Co. | Phenylacetonitrilehydroxyalkylaminoalkyl-ortho-substituted aryl compounds as immunosuppressives |
| US10144703B2 (en) | 2015-05-12 | 2018-12-04 | Piramal Enterprises Limited | Process for the preparation of Verapamil hydrochloride |
| WO2021245504A1 (fr) * | 2020-06-02 | 2021-12-09 | Glenmark Life Sciences Limited | Procédé de préparation de vérapamil |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1154810B (de) * | 1961-04-01 | 1963-09-26 | Knoll Ag | Verfahren zur Herstellung basisch substituierter Phenylacetonitrile |
| DE2631222C3 (de) * | 1976-07-12 | 1979-01-04 | Knoll Ag, 6700 Ludwigshafen | Verfahren zur Herstellung basisch substituierter Phenylacetonitrile |
-
1981
- 1981-06-02 DE DE19813121766 patent/DE3121766A1/de not_active Withdrawn
-
1982
- 1982-05-17 FI FI821735A patent/FI821735A0/fi not_active Application Discontinuation
- 1982-05-17 IL IL65807A patent/IL65807A0/xx unknown
- 1982-05-18 CA CA000403255A patent/CA1171430A/fr not_active Expired
- 1982-05-20 US US06/380,468 patent/US4418017A/en not_active Expired - Fee Related
- 1982-05-24 JP JP57086710A patent/JPS57200348A/ja active Pending
- 1982-05-26 EP EP82104575A patent/EP0066246A3/fr not_active Withdrawn
- 1982-05-28 ZA ZA823738A patent/ZA823738B/xx unknown
- 1982-05-31 YU YU01143/82A patent/YU114382A/xx unknown
- 1982-06-01 AU AU84368/82A patent/AU8436882A/en not_active Abandoned
- 1982-06-01 NO NO821817A patent/NO821817L/no unknown
- 1982-06-01 CS CS824052A patent/CS228932B2/cs unknown
- 1982-06-01 DK DK245682A patent/DK245682A/da unknown
Also Published As
| Publication number | Publication date |
|---|---|
| IL65807A0 (en) | 1982-08-31 |
| US4418017A (en) | 1983-11-29 |
| EP0066246A2 (fr) | 1982-12-08 |
| YU114382A (en) | 1985-03-20 |
| ZA823738B (en) | 1983-04-27 |
| DK245682A (da) | 1982-12-03 |
| CS228932B2 (en) | 1984-05-14 |
| DE3121766A1 (de) | 1982-12-16 |
| CA1171430A (fr) | 1984-07-24 |
| EP0066246A3 (fr) | 1984-02-01 |
| AU8436882A (en) | 1982-12-09 |
| JPS57200348A (en) | 1982-12-08 |
| FI821735A0 (fi) | 1982-05-17 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4614817A (en) | Making nitrodiarylamines | |
| JP2006232830A (ja) | 塩化アルキルの製法 | |
| Fields et al. | Preparation of Acetoxybenzyl Bromides | |
| NO821817L (no) | Fremgangsmaate for fremstilling av basisk substituert fenylacetonitriler. | |
| CN107501077A (zh) | 一种2‑(4‑溴甲基)苯基丙酸的制备方法 | |
| EP0027003B1 (fr) | Procédé de préparation d'une diarylamine | |
| CN104151342B (zh) | 一种合成联硼酸频那醇酯的方法 | |
| JPH03106848A (ja) | α―フルオロアクリロイル誘導体の製造方法 | |
| CA1093097A (fr) | Traduction non-disponible | |
| JPS5925779B2 (ja) | 立体異性脂環ジアミンの異性化法 | |
| EP0148145B1 (fr) | Procédé pour la préparation de nitrodiarylamines | |
| US6353126B1 (en) | Process for the production of malononitrile | |
| CN110003023B (zh) | 一种环境友好的n,n-二甲基甲酰胺二甲缩醛制备方法 | |
| Chambers et al. | The Dealkylation of Aromatic Amines | |
| JP4432172B2 (ja) | 第３級−ブトキシベンゼン誘導体の製造方法 | |
| JPS6227059B2 (fr) | ||
| CN112004806A (zh) | 制备3,4-二氯-n-(2-氰基苯基)-5-异噻唑甲酰胺的方法 | |
| WO2007107818A2 (fr) | Procede pour la preparation de 3,5-bis (trifluoromethyl)-n-methylbenzylamine | |
| EP0088383B1 (fr) | Procédé pour la préparation de 1-méthoxy-6-chloro-hexyne-2 | |
| CN111699172B (zh) | 三氟甲硫基烷基化合物的制造方法和三氟甲硫基卤烷化合物的组合物 | |
| SMITH et al. | Convenient Syntheses of 1, 2, 3, 4-Tetrahydroquinoxalines | |
| JP2594826B2 (ja) | ｐ−またはｍ−ヒドロキシフェネチルアルコールの製造法 | |
| CN113402452B (zh) | 一种制备2-氯-5-取代吡啶的方法 | |
| EP0519235A1 (fr) | Préparation d'amides d'acide alkylsulfonique | |
| US3222396A (en) | Process for the preparation of 4-halobutane-1-sulfonyl halides |