CA1154023A - Methode de preparation d'un derive d'imidazole - Google Patents
Methode de preparation d'un derive d'imidazoleInfo
- Publication number
- CA1154023A CA1154023A CA000368285A CA368285A CA1154023A CA 1154023 A CA1154023 A CA 1154023A CA 000368285 A CA000368285 A CA 000368285A CA 368285 A CA368285 A CA 368285A CA 1154023 A CA1154023 A CA 1154023A
- Authority
- CA
- Canada
- Prior art keywords
- formula
- thiomethyl
- quaternary
- preparing
- methyl
- 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
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 7
- 150000002460 imidazoles Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 11
- 125000005843 halogen group Chemical group 0.000 claims abstract description 5
- 150000003839 salts Chemical class 0.000 claims abstract description 5
- 239000002253 acid Substances 0.000 claims abstract description 4
- 150000004714 phosphonium salts Chemical group 0.000 claims abstract description 4
- 125000001453 quaternary ammonium group Chemical group 0.000 claims abstract description 4
- 239000007864 aqueous solution Substances 0.000 claims abstract description 3
- 239000002585 base Substances 0.000 claims abstract description 3
- 125000001246 bromo group Chemical group Br* 0.000 claims abstract description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims abstract description 3
- 239000012074 organic phase Substances 0.000 claims abstract description 3
- 239000003444 phase transfer catalyst Substances 0.000 claims abstract description 3
- JEOZNMMOIBLWLV-UHFFFAOYSA-N 2-[(5-methyl-1h-imidazol-4-yl)methylsulfanyl]ethanamine Chemical compound CC=1N=CNC=1CSCCN JEOZNMMOIBLWLV-UHFFFAOYSA-N 0.000 claims abstract 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract 2
- 229910052783 alkali metal Chemical group 0.000 claims abstract 2
- 150000001340 alkali metals Chemical group 0.000 claims abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 2
- 239000001257 hydrogen Substances 0.000 claims abstract 2
- 238000000034 method Methods 0.000 claims description 10
- HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 claims description 9
- 238000006243 chemical reaction Methods 0.000 claims description 9
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 6
- 239000000243 solution Substances 0.000 claims description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 4
- XKBGEWXEAPTVCK-UHFFFAOYSA-M methyltrioctylammonium chloride Chemical compound [Cl-].CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC XKBGEWXEAPTVCK-UHFFFAOYSA-M 0.000 claims description 4
- 150000001298 alcohols Chemical class 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- RYVBINGWVJJDPU-UHFFFAOYSA-M tributyl(hexadecyl)phosphanium;bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[P+](CCCC)(CCCC)CCCC RYVBINGWVJJDPU-UHFFFAOYSA-M 0.000 claims description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 5
- 125000000066 S-methyl group Chemical group [H]C([H])([H])S* 0.000 description 4
- RAXXELZNTBOGNW-UHFFFAOYSA-N 1H-imidazole Chemical class C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- VKPPFDPXZWFDFA-UHFFFAOYSA-N 2-chloroethanamine Chemical compound NCCCl VKPPFDPXZWFDFA-UHFFFAOYSA-N 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- UFULAYFCSOUIOV-UHFFFAOYSA-N cysteamine Chemical compound NCCS UFULAYFCSOUIOV-UHFFFAOYSA-N 0.000 description 3
- 229960003151 mercaptamine Drugs 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- -1 5-methyl-4-imidazolyl Chemical group 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 125000003277 amino group Chemical group 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- AXJZCJSXNZZMDU-UHFFFAOYSA-N (5-methyl-1h-imidazol-4-yl)methanol Chemical group CC=1N=CNC=1CO AXJZCJSXNZZMDU-UHFFFAOYSA-N 0.000 description 1
- ZOHLKTFCEUOOOQ-UHFFFAOYSA-N 4-(methoxymethyl)-5-methyl-1h-imidazole Chemical compound COCC=1N=CNC=1C ZOHLKTFCEUOOOQ-UHFFFAOYSA-N 0.000 description 1
- MLLYSQGRMFTIIZ-UHFFFAOYSA-N 5-(methylsulfanylmethyl)-1h-imidazole Chemical compound CSCC1=CN=CN1 MLLYSQGRMFTIIZ-UHFFFAOYSA-N 0.000 description 1
- 102000003710 Histamine H2 Receptors Human genes 0.000 description 1
- 108090000050 Histamine H2 Receptors Proteins 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 239000000739 antihistaminic agent Substances 0.000 description 1
- USFRYJRPHFMVBZ-UHFFFAOYSA-M benzyl(triphenyl)phosphanium;chloride Chemical compound [Cl-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)CC1=CC=CC=C1 USFRYJRPHFMVBZ-UHFFFAOYSA-M 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 238000006698 hydrazinolysis reaction Methods 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 125000005543 phthalimide group Chemical group 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- HYHCSLBZRBJJCH-UHFFFAOYSA-M sodium hydrosulfide Chemical compound [Na+].[SH-] HYHCSLBZRBJJCH-UHFFFAOYSA-M 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 230000003407 synthetizing effect Effects 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- NNENFOSYDBTCBO-UHFFFAOYSA-M tributyl(hexadecyl)phosphanium;chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCC[P+](CCCC)(CCCC)CCCC NNENFOSYDBTCBO-UHFFFAOYSA-M 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Plural Heterocyclic Compounds (AREA)
- Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| YUP80/80 | 1980-01-14 | ||
| YU80/80A YU41689B (en) | 1980-01-14 | 1980-01-14 | Process for preparing imidazole derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1154023A true CA1154023A (fr) | 1983-09-20 |
Family
ID=25548243
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000368285A Expired CA1154023A (fr) | 1980-01-14 | 1981-01-12 | Methode de preparation d'un derive d'imidazole |
Country Status (10)
| Country | Link |
|---|---|
| JP (1) | JPS56127361A (fr) |
| CA (1) | CA1154023A (fr) |
| CS (1) | CS214847B2 (fr) |
| FI (1) | FI804056L (fr) |
| HU (1) | HU187289B (fr) |
| NO (1) | NO810083L (fr) |
| PL (1) | PL129291B1 (fr) |
| SE (1) | SE8100127L (fr) |
| SU (1) | SU969159A3 (fr) |
| YU (1) | YU41689B (fr) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS58188860A (ja) * | 1982-04-27 | 1983-11-04 | Fujimoto Seiyaku Kk | イミダゾ−ル誘導体の製造方法 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5440547A (en) * | 1977-09-07 | 1979-03-30 | Seikosha Kk | Device for adjusting output frequency of frequency divider |
| IL56265A (en) * | 1977-12-28 | 1982-08-31 | Om Lab Sa | Process for preparing imidazolyl methylthio guanidine derivatives and a novel intermediate therefor |
-
1980
- 1980-01-14 YU YU80/80A patent/YU41689B/xx unknown
- 1980-12-30 FI FI804056A patent/FI804056L/fi not_active Application Discontinuation
-
1981
- 1981-01-12 NO NO810083A patent/NO810083L/no unknown
- 1981-01-12 CS CS81233A patent/CS214847B2/cs unknown
- 1981-01-12 SE SE8100127A patent/SE8100127L/xx not_active Application Discontinuation
- 1981-01-12 CA CA000368285A patent/CA1154023A/fr not_active Expired
- 1981-01-12 PL PL1981229185A patent/PL129291B1/pl unknown
- 1981-01-13 HU HU8171A patent/HU187289B/hu unknown
- 1981-01-13 JP JP275181A patent/JPS56127361A/ja active Pending
- 1981-01-13 SU SU813230706A patent/SU969159A3/ru active
Also Published As
| Publication number | Publication date |
|---|---|
| NO810083L (no) | 1981-07-15 |
| YU8080A (en) | 1983-10-31 |
| CS214847B2 (en) | 1982-06-25 |
| SU969159A3 (ru) | 1982-10-23 |
| FI804056L (fi) | 1981-07-15 |
| HU187289B (en) | 1985-12-28 |
| PL229185A1 (fr) | 1981-09-18 |
| SE8100127L (sv) | 1981-07-15 |
| YU41689B (en) | 1987-12-31 |
| PL129291B1 (en) | 1984-04-30 |
| JPS56127361A (en) | 1981-10-06 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |