DE2538621C2 - Verfahren zur Herstellung von 4-(Hydroxymethyl)-imidazolderivaten - Google Patents
Verfahren zur Herstellung von 4-(Hydroxymethyl)-imidazolderivatenInfo
- Publication number
- DE2538621C2 DE2538621C2 DE2538621A DE2538621A DE2538621C2 DE 2538621 C2 DE2538621 C2 DE 2538621C2 DE 2538621 A DE2538621 A DE 2538621A DE 2538621 A DE2538621 A DE 2538621A DE 2538621 C2 DE2538621 C2 DE 2538621C2
- Authority
- DE
- Germany
- Prior art keywords
- cathode
- acid
- hydroxymethyl
- solution
- preparation
- 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 12
- QDYTUZCWBJRHKK-UHFFFAOYSA-N imidazole-4-methanol Chemical class OCC1=CNC=N1 QDYTUZCWBJRHKK-UHFFFAOYSA-N 0.000 title claims description 7
- 238000002360 preparation method Methods 0.000 title claims description 5
- 239000000243 solution Substances 0.000 description 17
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- 150000001875 compounds Chemical class 0.000 description 10
- NKWCGTOZTHZDHB-UHFFFAOYSA-N 1h-imidazol-1-ium-4-carboxylate Chemical class OC(=O)C1=CNC=N1 NKWCGTOZTHZDHB-UHFFFAOYSA-N 0.000 description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 8
- 229910052739 hydrogen Inorganic materials 0.000 description 8
- 239000001257 hydrogen Substances 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- 239000002253 acid Substances 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- -1 alkyl radical Chemical class 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- 239000003586 protic polar solvent Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- 239000003792 electrolyte Substances 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 3
- 229910052753 mercury Inorganic materials 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 2
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000003957 anion exchange resin Substances 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 238000005868 electrolysis reaction Methods 0.000 description 2
- 125000004494 ethyl ester group Chemical group 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
- RIUZCJIFIIOBEZ-UHFFFAOYSA-N (4-butyl-1h-imidazol-5-yl)methanol Chemical compound CCCCC=1N=CNC=1CO RIUZCJIFIIOBEZ-UHFFFAOYSA-N 0.000 description 1
- AXJZCJSXNZZMDU-UHFFFAOYSA-N (5-methyl-1h-imidazol-4-yl)methanol Chemical compound CC=1N=CNC=1CO AXJZCJSXNZZMDU-UHFFFAOYSA-N 0.000 description 1
- KYWMCFOWDYFYLV-UHFFFAOYSA-N 1h-imidazole-2-carboxylic acid Chemical compound OC(=O)C1=NC=CN1 KYWMCFOWDYFYLV-UHFFFAOYSA-N 0.000 description 1
- NNWUEBIEOFQMSS-UHFFFAOYSA-N 2-Methylpiperidine Chemical compound CC1CCCCN1 NNWUEBIEOFQMSS-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- UGYXPZQILZRKJJ-UHFFFAOYSA-N 4-methylhistamine Chemical compound CC=1NC=NC=1CCN UGYXPZQILZRKJJ-UHFFFAOYSA-N 0.000 description 1
- BUDINVRUJUDSCN-UHFFFAOYSA-N 5-butyl-1h-imidazole-4-carboxylic acid Chemical compound CCCCC=1NC=NC=1C(O)=O BUDINVRUJUDSCN-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 229940122957 Histamine H2 receptor antagonist Drugs 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- PJPLGLBBGYAMRR-UHFFFAOYSA-N O.CC1=C(N=CN1)C(=O)O Chemical compound O.CC1=C(N=CN1)C(=O)O PJPLGLBBGYAMRR-UHFFFAOYSA-N 0.000 description 1
- SIOXPEMLGUPBBT-UHFFFAOYSA-N Picolinic acid Natural products OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 description 1
- 125000000066 S-methyl group Chemical group [H]C([H])([H])S* 0.000 description 1
- 239000000556 agonist Substances 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 239000000739 antihistaminic agent Substances 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 150000001559 benzoic acids Chemical class 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 1
- 229960001340 histamine Drugs 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229940075930 picrate Drugs 0.000 description 1
- OXNIZHLAWKMVMX-UHFFFAOYSA-M picrate anion Chemical compound [O-]C1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-M 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- VXKWYPOMXBVZSJ-UHFFFAOYSA-N tetramethyltin Chemical compound C[Sn](C)(C)C VXKWYPOMXBVZSJ-UHFFFAOYSA-N 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/64—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms, e.g. histidine
-
- C—CHEMISTRY; METALLURGY
- C25—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES; APPARATUS THEREFOR
- C25B—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES FOR THE PRODUCTION OF COMPOUNDS OR NON-METALS; APPARATUS THEREFOR
- C25B3/00—Electrolytic production of organic compounds
- C25B3/20—Processes
- C25B3/25—Reduction
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Electrochemistry (AREA)
- Materials Engineering (AREA)
- Metallurgy (AREA)
- Electrolytic Production Of Non-Metals, Compounds, Apparatuses Therefor (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB38259/74A GB1530895A (en) | 1974-09-02 | 1974-09-02 | Electrochemical reduction of 4-imidazole carboxylic acids |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2538621A1 DE2538621A1 (de) | 1976-03-11 |
| DE2538621C2 true DE2538621C2 (de) | 1983-07-21 |
Family
ID=10402306
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2538621A Expired DE2538621C2 (de) | 1974-09-02 | 1975-08-29 | Verfahren zur Herstellung von 4-(Hydroxymethyl)-imidazolderivaten |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US3984293A (en, 2012) |
| JP (1) | JPS5759313B2 (en, 2012) |
| BE (1) | BE832660A (en, 2012) |
| CA (1) | CA1058620A (en, 2012) |
| CH (1) | CH594631A5 (en, 2012) |
| DE (1) | DE2538621C2 (en, 2012) |
| DK (1) | DK388075A (en, 2012) |
| FR (1) | FR2287526A1 (en, 2012) |
| GB (1) | GB1530895A (en, 2012) |
| HU (1) | HU170220B (en, 2012) |
| IE (1) | IE42753B1 (en, 2012) |
| IL (1) | IL47926A (en, 2012) |
| LU (1) | LU73278A1 (en, 2012) |
| NL (1) | NL7510343A (en, 2012) |
| YU (1) | YU207575A (en, 2012) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4055573A (en) * | 1976-05-06 | 1977-10-25 | Smithkline Corporation | Electrochemical reduction of imidazolecarboxylic esters |
| NO781300L (no) | 1977-04-20 | 1978-10-23 | Ici Ltd | Fremgangsmaate for fremstilling av fysiologisk aktive guanidinderivater |
| US4165378A (en) | 1977-04-20 | 1979-08-21 | Ici Americas Inc. | Guanidine derivatives of imidazoles and thiazoles |
| US4224452A (en) * | 1978-03-02 | 1980-09-23 | Ethyl Corporation | Method for preparing 4-hydroxymethyl imidazoles |
| DE3069889D1 (en) | 1979-01-18 | 1985-02-14 | Ici Plc | Guanidine derivatives, processes for their manufacture and pharmaceutical compositions containing them |
| US4322539A (en) * | 1979-06-25 | 1982-03-30 | Ethyl Corporation | Conversion of ethers to thioamines |
| US4968588A (en) * | 1986-01-30 | 1990-11-06 | Fuji Photo Film Co., Ltd. | Method for processing silver halide color photographic materials with a color developer comprising no benzyl alcohol and an accelerator |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US815193A (en) * | 1905-10-11 | 1906-03-13 | Basf Ag | Production of aromatic alcohols. |
-
1974
- 1974-09-02 GB GB38259/74A patent/GB1530895A/en not_active Expired
-
1975
- 1975-08-06 US US05/602,332 patent/US3984293A/en not_active Expired - Lifetime
- 1975-08-08 IE IE1781/75A patent/IE42753B1/en unknown
- 1975-08-13 YU YU02075/75A patent/YU207575A/xx unknown
- 1975-08-15 IL IL47926A patent/IL47926A/xx unknown
- 1975-08-20 CA CA233,791A patent/CA1058620A/en not_active Expired
- 1975-08-22 BE BE159390A patent/BE832660A/xx not_active IP Right Cessation
- 1975-08-28 CH CH1116275A patent/CH594631A5/xx not_active IP Right Cessation
- 1975-08-28 DK DK388075A patent/DK388075A/da not_active Application Discontinuation
- 1975-08-28 FR FR7526533A patent/FR2287526A1/fr active Granted
- 1975-08-29 LU LU73278A patent/LU73278A1/xx unknown
- 1975-08-29 DE DE2538621A patent/DE2538621C2/de not_active Expired
- 1975-09-01 JP JP50106457A patent/JPS5759313B2/ja not_active Expired
- 1975-09-01 HU HUSI1487A patent/HU170220B/hu unknown
- 1975-09-02 NL NL7510343A patent/NL7510343A/xx not_active Application Discontinuation
Non-Patent Citations (1)
| Title |
|---|
| NICHTS-ERMITTELT |
Also Published As
| Publication number | Publication date |
|---|---|
| LU73278A1 (en, 2012) | 1976-04-13 |
| DK388075A (da) | 1976-03-03 |
| JPS5759313B2 (en, 2012) | 1982-12-14 |
| DE2538621A1 (de) | 1976-03-11 |
| US3984293A (en) | 1976-10-05 |
| BE832660A (fr) | 1976-02-23 |
| JPS5154560A (en, 2012) | 1976-05-13 |
| NL7510343A (nl) | 1976-03-04 |
| HU170220B (en, 2012) | 1977-04-28 |
| IL47926A0 (en) | 1975-11-25 |
| CA1058620A (en) | 1979-07-17 |
| IL47926A (en) | 1980-10-26 |
| IE42753L (en) | 1976-03-02 |
| FR2287526B1 (en, 2012) | 1979-05-25 |
| GB1530895A (en) | 1978-11-01 |
| YU207575A (en) | 1982-02-28 |
| FR2287526A1 (fr) | 1976-05-07 |
| CH594631A5 (en, 2012) | 1978-01-13 |
| IE42753B1 (en) | 1980-10-08 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| 8125 | Change of the main classification |
Ipc: C25B 3/04 |
|
| 8126 | Change of the secondary classification |
Ipc: C07D233/64 |
|
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |