CS214847B2 - Method of making the 4-+l +l2.aminoethyl+p-5-methylimidazole - Google Patents
Method of making the 4-+l +l2.aminoethyl+p-5-methylimidazole Download PDFInfo
- Publication number
- CS214847B2 CS214847B2 CS81233A CS23381A CS214847B2 CS 214847 B2 CS214847 B2 CS 214847B2 CS 81233 A CS81233 A CS 81233A CS 23381 A CS23381 A CS 23381A CS 214847 B2 CS214847 B2 CS 214847B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- formula
- aminoethyl
- thiomethyl
- reaction
- methylimidazole
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title abstract description 4
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 title abstract 3
- 150000003839 salts Chemical class 0.000 claims abstract description 6
- 239000002253 acid Substances 0.000 claims abstract description 5
- 229910052783 alkali metal Chemical group 0.000 claims abstract description 4
- 150000004714 phosphonium salts Chemical group 0.000 claims abstract description 4
- 150000001340 alkali metals Chemical group 0.000 claims abstract description 3
- 239000007864 aqueous solution Substances 0.000 claims abstract description 3
- 239000002585 base Substances 0.000 claims abstract description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 3
- 239000001257 hydrogen Substances 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
- 238000000034 method Methods 0.000 claims description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 12
- 238000006243 chemical reaction Methods 0.000 claims description 11
- 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 8
- JEOZNMMOIBLWLV-UHFFFAOYSA-N 2-[(5-methyl-1h-imidazol-4-yl)methylsulfanyl]ethanamine Chemical compound CC=1N=CNC=1CSCCN JEOZNMMOIBLWLV-UHFFFAOYSA-N 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 5
- 239000000243 solution Substances 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- 150000001298 alcohols Chemical class 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- XKBGEWXEAPTVCK-UHFFFAOYSA-M methyltrioctylammonium chloride Chemical compound [Cl-].CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC XKBGEWXEAPTVCK-UHFFFAOYSA-M 0.000 claims description 2
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims 2
- BXIZTHHOWAEARP-UHFFFAOYSA-N [Br-].C(CCC)[PH+](CCCC)CCCC.C(CCC)[PH+](CCCC)CCCC.C(CCC)[PH+](CCCC)CCCC.C(CCC)[PH+](CCCC)CCCC.C(CCC)[PH+](CCCC)CCCC.C(CCC)[PH+](CCCC)CCCC.[Br-].[Br-].[Br-].[Br-].[Br-] Chemical compound [Br-].C(CCC)[PH+](CCCC)CCCC.C(CCC)[PH+](CCCC)CCCC.C(CCC)[PH+](CCCC)CCCC.C(CCC)[PH+](CCCC)CCCC.C(CCC)[PH+](CCCC)CCCC.C(CCC)[PH+](CCCC)CCCC.[Br-].[Br-].[Br-].[Br-].[Br-] BXIZTHHOWAEARP-UHFFFAOYSA-N 0.000 claims 1
- 239000003960 organic solvent Substances 0.000 claims 1
- 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 1
- 150000001875 compounds Chemical class 0.000 abstract description 10
- 125000001453 quaternary ammonium group Chemical group 0.000 abstract description 2
- 125000000066 S-methyl group Chemical group [H]C([H])([H])S* 0.000 abstract 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 125000001246 bromo group Chemical group Br* 0.000 abstract 1
- 125000001309 chloro group Chemical group Cl* 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- VKPPFDPXZWFDFA-UHFFFAOYSA-N 2-chloroethanamine Chemical compound NCCCl VKPPFDPXZWFDFA-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-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
- GCYDEHNKSNMNMN-UHFFFAOYSA-N (5-methyl-1h-imidazol-4-yl)methanethiol Chemical compound CC=1NC=NC=1CS GCYDEHNKSNMNMN-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 2
- -1 alkali metal salt Chemical class 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- HUYXJSWOXHSOPB-UHFFFAOYSA-N Cl.CCCCCCCCC(N)=O Chemical compound Cl.CCCCCCCCC(N)=O HUYXJSWOXHSOPB-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-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
- 239000013543 active substance 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
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- CCGSUNCLSOWKJO-UHFFFAOYSA-N cimetidine Chemical compound N#CNC(=N/C)\NCCSCC1=NC=N[C]1C CCGSUNCLSOWKJO-UHFFFAOYSA-N 0.000 description 1
- 229960001380 cimetidine Drugs 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 229960001340 histamine Drugs 0.000 description 1
- 238000006698 hydrazinolysis reaction Methods 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 125000005544 phthalimido 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
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- RYVBINGWVJJDPU-UHFFFAOYSA-M tributyl(hexadecyl)phosphanium;bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[P+](CCCC)(CCCC)CCCC RYVBINGWVJJDPU-UHFFFAOYSA-M 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 (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| YU80/80A YU41689B (en) | 1980-01-14 | 1980-01-14 | Process for preparing imidazole derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS214847B2 true CS214847B2 (en) | 1982-06-25 |
Family
ID=25548243
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS81233A CS214847B2 (en) | 1980-01-14 | 1981-01-12 | Method of making the 4-+l +l2.aminoethyl+p-5-methylimidazole |
Country Status (10)
| Country | Link |
|---|---|
| JP (1) | JPS56127361A (ru) |
| CA (1) | CA1154023A (ru) |
| CS (1) | CS214847B2 (ru) |
| FI (1) | FI804056L (ru) |
| HU (1) | HU187289B (ru) |
| NO (1) | NO810083L (ru) |
| PL (1) | PL129291B1 (ru) |
| SE (1) | SE8100127L (ru) |
| SU (1) | SU969159A3 (ru) |
| YU (1) | YU41689B (ru) |
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 PL PL1981229185A patent/PL129291B1/pl unknown
- 1981-01-12 SE SE8100127A patent/SE8100127L/xx not_active Application Discontinuation
- 1981-01-12 NO NO810083A patent/NO810083L/no unknown
- 1981-01-12 CS CS81233A patent/CS214847B2/cs unknown
- 1981-01-12 CA CA000368285A patent/CA1154023A/en not_active Expired
- 1981-01-13 SU SU813230706A patent/SU969159A3/ru active
- 1981-01-13 HU HU8171A patent/HU187289B/hu unknown
- 1981-01-13 JP JP275181A patent/JPS56127361A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| CA1154023A (en) | 1983-09-20 |
| YU8080A (en) | 1983-10-31 |
| PL129291B1 (en) | 1984-04-30 |
| SU969159A3 (ru) | 1982-10-23 |
| YU41689B (en) | 1987-12-31 |
| SE8100127L (sv) | 1981-07-15 |
| NO810083L (no) | 1981-07-15 |
| PL229185A1 (ru) | 1981-09-18 |
| JPS56127361A (en) | 1981-10-06 |
| FI804056L (fi) | 1981-07-15 |
| HU187289B (en) | 1985-12-28 |
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