DE2226588C3 - Verfahren zur Herstellung von N-(2-Cyanoäthyl)- oder N,N-Bis-(2-Cyanoäthyl)-aminophenolen - Google Patents
Verfahren zur Herstellung von N-(2-Cyanoäthyl)- oder N,N-Bis-(2-Cyanoäthyl)-aminophenolenInfo
- Publication number
- DE2226588C3 DE2226588C3 DE2226588A DE2226588A DE2226588C3 DE 2226588 C3 DE2226588 C3 DE 2226588C3 DE 2226588 A DE2226588 A DE 2226588A DE 2226588 A DE2226588 A DE 2226588A DE 2226588 C3 DE2226588 C3 DE 2226588C3
- Authority
- DE
- Germany
- Prior art keywords
- cyanoethyl
- aminophenol
- acrylonitrile
- bis
- aminophenols
- 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
- 238000000034 method Methods 0.000 title claims description 24
- HBZUTHNXOTWAFZ-UHFFFAOYSA-N 3-[n-(2-cyanoethyl)-2-hydroxyanilino]propanenitrile Chemical class OC1=CC=CC=C1N(CCC#N)CCC#N HBZUTHNXOTWAFZ-UHFFFAOYSA-N 0.000 title claims description 5
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 title description 7
- 238000002360 preparation method Methods 0.000 title description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 31
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 19
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 description 18
- 239000000047 product Substances 0.000 description 13
- CWLKGDAVCFYWJK-UHFFFAOYSA-N 3-aminophenol Chemical compound NC1=CC=CC(O)=C1 CWLKGDAVCFYWJK-UHFFFAOYSA-N 0.000 description 12
- 239000000243 solution Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 239000012043 crude product Substances 0.000 description 7
- VPINVLFFKHNQBR-UHFFFAOYSA-N 3-(4-hydroxyanilino)propanenitrile Chemical compound OC1=CC=C(NCCC#N)C=C1 VPINVLFFKHNQBR-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 239000013078 crystal Substances 0.000 description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 4
- -1 alkali metal salt Chemical class 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 229940018563 3-aminophenol Drugs 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000007278 cyanoethylation reaction Methods 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical class CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- MBEVBCXNFSOBBZ-UHFFFAOYSA-N 3-(2-hydroxyanilino)propanenitrile Chemical compound OC1=CC=CC=C1NCCC#N MBEVBCXNFSOBBZ-UHFFFAOYSA-N 0.000 description 2
- JCBVUSXYPSJVSB-UHFFFAOYSA-N 3-(3-hydroxyanilino)propanenitrile Chemical compound OC1=CC=CC(NCCC#N)=C1 JCBVUSXYPSJVSB-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- NRQGKJCYSBOWBS-UHFFFAOYSA-N N.NC1=C(C=CC=C1)O Chemical compound N.NC1=C(C=CC=C1)O NRQGKJCYSBOWBS-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 150000004982 aromatic amines Chemical class 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 description 2
- 229940031826 phenolate Drugs 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- ZKZPGKMLMRIDJQ-UHFFFAOYSA-N 3-[N-(2-cyanoethyl)-4-hydroxyanilino]propanenitrile Chemical group OC1=CC=C(C=C1)N(CCC#N)CCC#N ZKZPGKMLMRIDJQ-UHFFFAOYSA-N 0.000 description 1
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-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
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 1
- NCBBSEAYIIQQQU-UHFFFAOYSA-N OC1=CC=CC(=C1)N(CCC#N)CCC#N Chemical group OC1=CC=CC(=C1)N(CCC#N)CCC#N NCBBSEAYIIQQQU-UHFFFAOYSA-N 0.000 description 1
- 101150046432 Tril gene Proteins 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 description 1
- 229960001231 choline Drugs 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940082150 encore Drugs 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
- 239000012442 inert solvent Substances 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- MNBARIDWGOFKTJ-UHFFFAOYSA-M potassium;2-aminophenolate Chemical class [K+].NC1=CC=CC=C1[O-] MNBARIDWGOFKTJ-UHFFFAOYSA-M 0.000 description 1
- ZGJADVGJIVEEGF-UHFFFAOYSA-M potassium;phenoxide Chemical compound [K+].[O-]C1=CC=CC=C1 ZGJADVGJIVEEGF-UHFFFAOYSA-M 0.000 description 1
- 125000003263 primary aromatic amine group Chemical group 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 150000003336 secondary aromatic amines Chemical class 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000002459 sustained effect Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- YLKXGVSMBYZCSB-UHFFFAOYSA-N trimethylazanium;phenoxide Chemical compound CN(C)C.OC1=CC=CC=C1 YLKXGVSMBYZCSB-UHFFFAOYSA-N 0.000 description 1
- 239000002699 waste material Substances 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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US14898871A | 1971-06-01 | 1971-06-01 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2226588A1 DE2226588A1 (de) | 1972-12-14 |
| DE2226588B2 DE2226588B2 (de) | 1981-04-09 |
| DE2226588C3 true DE2226588C3 (de) | 1982-01-28 |
Family
ID=22528317
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2226588A Expired DE2226588C3 (de) | 1971-06-01 | 1972-05-31 | Verfahren zur Herstellung von N-(2-Cyanoäthyl)- oder N,N-Bis-(2-Cyanoäthyl)-aminophenolen |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US3743668A (https=) |
| JP (1) | JPS5614658B1 (https=) |
| BE (1) | BE784203A (https=) |
| CA (1) | CA956648A (https=) |
| CH (1) | CH574398A5 (https=) |
| DE (1) | DE2226588C3 (https=) |
| FR (1) | FR2141151A5 (https=) |
| GB (1) | GB1338522A (https=) |
| IT (1) | IT1035523B (https=) |
| NL (1) | NL7207341A (https=) |
| SE (1) | SE370696B (https=) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3890368A (en) * | 1973-06-21 | 1975-06-17 | Mallinckrodt Inc | Method for N,N-dicyanoethylating aminophenols |
| DE3520982A1 (de) * | 1985-06-12 | 1986-12-18 | Basf Ag, 6700 Ludwigshafen | Verfahren zur herstellung von 2-(n-formylamino)-propionitril |
| US4835180A (en) * | 1986-10-02 | 1989-05-30 | Sterling Drug Inc. | N-(ω-cyanoalkyl)aminophenols and use as inhibitors of lipoxygenase activity |
| DE4303131A1 (de) * | 1993-02-04 | 1994-08-11 | Bayer Ag | Verfahren zur Herstellung von Mono-N-beta-cyanoethylanilinen |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH397712A (de) * | 1961-08-04 | 1965-08-31 | Geigy Ag J R | Verfahren zur Cyanäthylierung primärer und sekundärer aromatischer Amine |
-
1971
- 1971-06-01 US US00148988A patent/US3743668A/en not_active Expired - Lifetime
-
1972
- 1972-05-23 GB GB2425772A patent/GB1338522A/en not_active Expired
- 1972-05-24 IT IT50467/72A patent/IT1035523B/it active
- 1972-05-24 CA CA142,892A patent/CA956648A/en not_active Expired
- 1972-05-29 CH CH793972A patent/CH574398A5/xx not_active IP Right Cessation
- 1972-05-31 DE DE2226588A patent/DE2226588C3/de not_active Expired
- 1972-05-31 SE SE7207145A patent/SE370696B/xx unknown
- 1972-05-31 NL NL7207341A patent/NL7207341A/xx not_active Application Discontinuation
- 1972-05-31 BE BE784203A patent/BE784203A/xx not_active IP Right Cessation
- 1972-05-31 JP JP5421272A patent/JPS5614658B1/ja active Pending
- 1972-06-01 FR FR7219765A patent/FR2141151A5/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| IT1035523B (it) | 1979-10-20 |
| CH574398A5 (https=) | 1976-04-15 |
| US3743668A (en) | 1973-07-03 |
| NL7207341A (https=) | 1972-12-05 |
| DE2226588A1 (de) | 1972-12-14 |
| DE2226588B2 (de) | 1981-04-09 |
| SE370696B (https=) | 1974-10-28 |
| JPS5614658B1 (https=) | 1981-04-06 |
| FR2141151A5 (https=) | 1973-01-19 |
| BE784203A (fr) | 1972-11-30 |
| CA956648A (en) | 1974-10-22 |
| GB1338522A (en) | 1973-11-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OD | Request for examination | ||
| OGA | New person/name/address of the applicant | ||
| C3 | Grant after two publication steps (3rd publication) | ||
| 8339 | Ceased/non-payment of the annual fee |