CS202001B2 - Process for preparing derivative of imidazole - Google Patents
Process for preparing derivative of imidazole Download PDFInfo
- Publication number
- CS202001B2 CS202001B2 CS48576A CS48576A CS202001B2 CS 202001 B2 CS202001 B2 CS 202001B2 CS 48576 A CS48576 A CS 48576A CS 48576 A CS48576 A CS 48576A CS 202001 B2 CS202001 B2 CS 202001B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- parts
- imidazole
- dichlorophenyl
- ylmethyl
- dioxolane
- Prior art date
Links
- 150000002460 imidazoles Chemical class 0.000 title claims description 18
- 238000004519 manufacturing process Methods 0.000 title claims description 7
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 177
- -1 halothienyl Chemical group 0.000 claims description 120
- 150000003839 salts Chemical class 0.000 claims description 95
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 68
- 239000002253 acid Substances 0.000 claims description 64
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims description 61
- 238000000034 method Methods 0.000 claims description 61
- 150000001875 compounds Chemical class 0.000 claims description 44
- 125000005997 bromomethyl group Chemical group 0.000 claims description 35
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 28
- 125000004432 carbon atom Chemical group C* 0.000 claims description 23
- 238000006243 chemical reaction Methods 0.000 claims description 18
- 229910052751 metal Chemical class 0.000 claims description 16
- 239000002184 metal Chemical class 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 14
- 238000002360 preparation method Methods 0.000 claims description 13
- 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 claims description 12
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 10
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- 150000002367 halogens Chemical class 0.000 claims description 8
- 125000001424 substituent group Chemical group 0.000 claims description 8
- 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 description 8
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
- 150000002148 esters Chemical class 0.000 claims description 7
- 239000003960 organic solvent Substances 0.000 claims description 7
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 7
- 235000011181 potassium carbonates Nutrition 0.000 claims description 7
- 239000004305 biphenyl Substances 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 230000015572 biosynthetic process Effects 0.000 claims description 5
- 125000001624 naphthyl group Chemical group 0.000 claims description 5
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 4
- 125000006331 halo benzoyl group Chemical group 0.000 claims description 4
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 4
- 229910001511 metal iodide Inorganic materials 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 230000003287 optical effect Effects 0.000 claims description 4
- 235000015497 potassium bicarbonate Nutrition 0.000 claims description 4
- 235000015424 sodium Nutrition 0.000 claims description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 4
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 4
- IRAFXGAHTMFJLR-UHFFFAOYSA-N 2-(bromomethyl)-4-[(4-bromophenoxy)methyl]-2-(2,4-dichlorophenyl)-1,3-dioxolane Chemical compound ClC1=CC(Cl)=CC=C1C1(CBr)OC(COC=2C=CC(Br)=CC=2)CO1 IRAFXGAHTMFJLR-UHFFFAOYSA-N 0.000 claims description 3
- 125000004849 alkoxymethyl group Chemical group 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000001544 thienyl group Chemical group 0.000 claims description 2
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims 1
- GNZHVEIGGFMLSP-UHFFFAOYSA-N 1-[[2-(2,4-dichlorophenyl)-4-[(4-phenylphenoxy)methyl]-1,3-dioxolan-2-yl]methyl]imidazole Chemical compound ClC1=CC(Cl)=CC=C1C1(CN2C=NC=C2)OC(COC=2C=CC(=CC=2)C=2C=CC=CC=2)CO1 GNZHVEIGGFMLSP-UHFFFAOYSA-N 0.000 claims 1
- WIZMVGOIBVVWHI-UHFFFAOYSA-N 1-[[2-(2,4-dichlorophenyl)-4-ethyl-1,3-dioxolan-2-yl]methyl]imidazole Chemical compound O1C(CC)COC1(C=1C(=CC(Cl)=CC=1)Cl)CN1C=NC=C1 WIZMVGOIBVVWHI-UHFFFAOYSA-N 0.000 claims 1
- AQJXVDWOEYEFCB-UHFFFAOYSA-N 1-[[2-(2-chloro-4-fluorophenyl)-4-ethyl-1,3-dioxolan-2-yl]methyl]imidazole Chemical compound O1C(CC)COC1(C=1C(=CC(F)=CC=1)Cl)CN1C=NC=C1 AQJXVDWOEYEFCB-UHFFFAOYSA-N 0.000 claims 1
- CXLVPVKGMHGKMB-UHFFFAOYSA-N 1-[[2-(4-bromo-2-chlorophenyl)-4-ethyl-1,3-dioxolan-2-yl]methyl]imidazole Chemical compound O1C(CC)COC1(C=1C(=CC(Br)=CC=1)Cl)CN1C=NC=C1 CXLVPVKGMHGKMB-UHFFFAOYSA-N 0.000 claims 1
- FGSKNRQPUTXJPG-UHFFFAOYSA-N 1-[[4-[(4-bromophenoxy)methyl]-2-(2,4-dichlorophenyl)-1,3-dioxolan-2-yl]methyl]imidazole Chemical compound ClC1=CC(Cl)=CC=C1C1(CN2C=NC=C2)OC(COC=2C=CC(Br)=CC=2)CO1 FGSKNRQPUTXJPG-UHFFFAOYSA-N 0.000 claims 1
- FJSKMXIPXNDQOG-UHFFFAOYSA-N 1-[[4-[(4-bromophenoxy)methyl]-2-(4-chlorophenyl)-1,3-dioxolan-2-yl]methyl]imidazole Chemical compound C1=CC(Cl)=CC=C1C1(CN2C=NC=C2)OC(COC=2C=CC(Br)=CC=2)CO1 FJSKMXIPXNDQOG-UHFFFAOYSA-N 0.000 claims 1
- LVWCKDSNNFNNTH-UHFFFAOYSA-N 2-(4-bromo-2-chlorophenyl)-4-ethyl-1,3-dioxolane Chemical compound BrC1=CC(=C(C=C1)C1OCC(O1)CC)Cl LVWCKDSNNFNNTH-UHFFFAOYSA-N 0.000 claims 1
- NPNHFVNLKKJVSS-UHFFFAOYSA-N 2-(bromomethyl)-2-(2,4-dichlorophenyl)-4-[(4-methoxyphenoxy)methyl]-1,3-dioxolane Chemical compound BrCC1(OCC(O1)COC1=CC=C(C=C1)OC)C1=C(C=C(C=C1)Cl)Cl NPNHFVNLKKJVSS-UHFFFAOYSA-N 0.000 claims 1
- IJFQVWIAHXOHTM-UHFFFAOYSA-N 2-(bromomethyl)-2-(2,4-dichlorophenyl)-4-[(4-phenylphenoxy)methyl]-1,3-dioxolane Chemical compound ClC1=CC(Cl)=CC=C1C1(CBr)OC(COC=2C=CC(=CC=2)C=2C=CC=CC=2)CO1 IJFQVWIAHXOHTM-UHFFFAOYSA-N 0.000 claims 1
- WVOHJAWNRZYVCS-UHFFFAOYSA-N 2-(bromomethyl)-2-(2,4-dichlorophenyl)-4-ethyl-1,3-dioxolane Chemical compound O1C(CC)COC1(CBr)C1=CC=C(Cl)C=C1Cl WVOHJAWNRZYVCS-UHFFFAOYSA-N 0.000 claims 1
- YDOYEJFHCXCCDZ-UHFFFAOYSA-N 2-(bromomethyl)-4-[(4-bromophenoxy)methyl]-2-(4-chlorophenyl)-1,3-dioxolane Chemical compound BrCC1(OCC(O1)COC1=CC=C(C=C1)Br)C1=CC=C(C=C1)Cl YDOYEJFHCXCCDZ-UHFFFAOYSA-N 0.000 claims 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- 125000004970 halomethyl group Chemical group 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 239000011593 sulfur Chemical group 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 120
- 239000000203 mixture Substances 0.000 description 109
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 109
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 93
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 69
- 229910017604 nitric acid Inorganic materials 0.000 description 69
- 239000000047 product Substances 0.000 description 62
- 239000000243 solution Substances 0.000 description 57
- 239000011541 reaction mixture Substances 0.000 description 55
- 239000003480 eluent Substances 0.000 description 53
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 52
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 44
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 41
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 40
- 239000000460 chlorine Substances 0.000 description 40
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 39
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 38
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 35
- 229960001701 chloroform Drugs 0.000 description 35
- 239000000284 extract Substances 0.000 description 35
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 34
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 32
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 31
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 30
- 239000002904 solvent Substances 0.000 description 28
- 239000007858 starting material Substances 0.000 description 28
- 150000002823 nitrates Chemical class 0.000 description 27
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 26
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 23
- 238000010898 silica gel chromatography Methods 0.000 description 23
- 239000000706 filtrate Substances 0.000 description 20
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Inorganic materials [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 17
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 15
- 238000010992 reflux Methods 0.000 description 15
- 230000000843 anti-fungal effect Effects 0.000 description 14
- VFNGKCDDZUSWLR-UHFFFAOYSA-L disulfate(2-) Chemical compound [O-]S(=O)(=O)OS([O-])(=O)=O VFNGKCDDZUSWLR-UHFFFAOYSA-L 0.000 description 14
- 230000000694 effects Effects 0.000 description 14
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 13
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 229940121375 antifungal agent Drugs 0.000 description 12
- 230000003385 bacteriostatic effect Effects 0.000 description 12
- 235000010290 biphenyl Nutrition 0.000 description 12
- 239000012258 stirred mixture Substances 0.000 description 12
- 238000003756 stirring Methods 0.000 description 12
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 11
- 238000002844 melting Methods 0.000 description 11
- 230000008018 melting Effects 0.000 description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 11
- 239000002585 base Substances 0.000 description 10
- 150000004862 dioxolanes Chemical group 0.000 description 10
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 10
- 239000000741 silica gel Substances 0.000 description 10
- 229910002027 silica gel Inorganic materials 0.000 description 10
- 229910002651 NO3 Inorganic materials 0.000 description 9
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Natural products OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 9
- 239000004480 active ingredient Substances 0.000 description 9
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 8
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 8
- 239000006185 dispersion Substances 0.000 description 8
- 239000007788 liquid Substances 0.000 description 8
- 239000003208 petroleum Substances 0.000 description 8
- 239000012312 sodium hydride Substances 0.000 description 8
- 229910000104 sodium hydride Inorganic materials 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- DASJDMQCPIDJIF-UHFFFAOYSA-N 2-bromo-1-(2,4-dichlorophenyl)ethanone Chemical compound ClC1=CC=C(C(=O)CBr)C(Cl)=C1 DASJDMQCPIDJIF-UHFFFAOYSA-N 0.000 description 7
- 241000894006 Bacteria Species 0.000 description 7
- 241000233866 Fungi Species 0.000 description 7
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 7
- 125000001309 chloro group Chemical group Cl* 0.000 description 7
- 239000000543 intermediate Substances 0.000 description 7
- 239000012074 organic phase Substances 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
- 230000000844 anti-bacterial effect Effects 0.000 description 6
- 239000002609 medium Substances 0.000 description 6
- 235000009518 sodium iodide Nutrition 0.000 description 6
- 238000009835 boiling Methods 0.000 description 5
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- 229910052708 sodium Inorganic materials 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- FLAYZKKEOIAALB-UHFFFAOYSA-N 2-bromo-1-(4-chlorophenyl)ethanone Chemical compound ClC1=CC=C(C(=O)CBr)C=C1 FLAYZKKEOIAALB-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
- 229910052794 bromium Inorganic materials 0.000 description 4
- 238000004587 chromatography analysis Methods 0.000 description 4
- 238000004140 cleaning Methods 0.000 description 4
- 239000000839 emulsion Substances 0.000 description 4
- 239000012442 inert solvent Substances 0.000 description 4
- 230000005764 inhibitory process Effects 0.000 description 4
- HRDXJKGNWSUIBT-UHFFFAOYSA-N methoxybenzene Chemical group [CH2]OC1=CC=CC=C1 HRDXJKGNWSUIBT-UHFFFAOYSA-N 0.000 description 4
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 description 3
- XKTYXVDYIKIYJP-UHFFFAOYSA-N 3h-dioxole Chemical compound C1OOC=C1 XKTYXVDYIKIYJP-UHFFFAOYSA-N 0.000 description 3
- KBIWNQVZKHSHTI-UHFFFAOYSA-N 4-n,4-n-dimethylbenzene-1,4-diamine;oxalic acid Chemical compound OC(=O)C(O)=O.CN(C)C1=CC=C(N)C=C1 KBIWNQVZKHSHTI-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 3
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Natural products OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 3
- 125000005998 bromoethyl group Chemical group 0.000 description 3
- 238000004440 column chromatography Methods 0.000 description 3
- 238000007796 conventional method Methods 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000010790 dilution Methods 0.000 description 3
- 239000012895 dilution Substances 0.000 description 3
- 239000002270 dispersing agent Substances 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 239000003995 emulsifying agent Substances 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 229910052740 iodine Inorganic materials 0.000 description 3
- 238000005907 ketalization reaction Methods 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 239000002674 ointment Substances 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- BOULDCYZLOKTGR-UHFFFAOYSA-N 1-(2-chloro-4-fluorophenyl)-2-imidazol-1-ylethanone;hydrochloride Chemical compound Cl.ClC1=CC(F)=CC=C1C(=O)CN1C=NC=C1 BOULDCYZLOKTGR-UHFFFAOYSA-N 0.000 description 2
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- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
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- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
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- 238000005507 spraying Methods 0.000 description 1
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- LACHTKPTWJUZBJ-UHFFFAOYSA-N sulfo hydrogen sulfate;hydrate Chemical compound O.OS(=O)(=O)OS(O)(=O)=O LACHTKPTWJUZBJ-UHFFFAOYSA-N 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
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- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/544,157 US3936470A (en) | 1975-01-27 | 1975-01-27 | 1,3-Dioxolan-2-ylmethylimidazoles |
| US61986375A | 1975-10-06 | 1975-10-06 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS202001B2 true CS202001B2 (en) | 1980-12-31 |
Family
ID=27067525
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS48576A CS202001B2 (en) | 1975-01-27 | 1976-01-26 | Process for preparing derivative of imidazole |
Country Status (14)
| Country | Link |
|---|---|
| CS (1) | CS202001B2 (OSRAM) |
| DK (1) | DK157300C (OSRAM) |
| ES (1) | ES444667A1 (OSRAM) |
| FI (1) | FI62081C (OSRAM) |
| HU (1) | HU174593B (OSRAM) |
| IE (1) | IE43157B1 (OSRAM) |
| IL (1) | IL48902A (OSRAM) |
| MX (1) | MX3143E (OSRAM) |
| NZ (1) | NZ179231A (OSRAM) |
| PH (1) | PH13605A (OSRAM) |
| PL (1) | PL101460B1 (OSRAM) |
| PT (1) | PT64741B (OSRAM) |
| SU (1) | SU850006A3 (OSRAM) |
| YU (1) | YU39956B (OSRAM) |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3575999A (en) * | 1968-08-19 | 1971-04-20 | Janssen Pharmaceutica Nv | Ketal derivatives of imidazole |
-
1975
- 1975-11-12 NZ NZ17923175A patent/NZ179231A/xx unknown
- 1975-12-03 MX MX46175U patent/MX3143E/es unknown
- 1975-12-29 PH PH17929A patent/PH13605A/en unknown
-
1976
- 1976-01-15 YU YU11276A patent/YU39956B/xx unknown
- 1976-01-21 SU SU762312703A patent/SU850006A3/ru active
- 1976-01-26 IE IE13976A patent/IE43157B1/en unknown
- 1976-01-26 FI FI760175A patent/FI62081C/fi not_active IP Right Cessation
- 1976-01-26 PL PL18681476A patent/PL101460B1/pl unknown
- 1976-01-26 HU HU76JA748A patent/HU174593B/hu not_active IP Right Cessation
- 1976-01-26 DK DK30276A patent/DK157300C/da not_active IP Right Cessation
- 1976-01-26 IL IL48902A patent/IL48902A/xx unknown
- 1976-01-26 PT PT6474176A patent/PT64741B/pt unknown
- 1976-01-26 CS CS48576A patent/CS202001B2/cs unknown
- 1976-01-27 ES ES444667A patent/ES444667A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| IE43157B1 (en) | 1980-12-31 |
| DK157300B (da) | 1989-12-04 |
| IL48902A0 (en) | 1976-03-31 |
| PL101460B1 (pl) | 1978-12-30 |
| MX3143E (es) | 1980-05-09 |
| YU11276A (en) | 1983-01-21 |
| SU850006A3 (ru) | 1981-07-23 |
| DK30276A (da) | 1976-07-28 |
| PT64741B (fr) | 1978-01-04 |
| HU174593B (hu) | 1980-02-28 |
| YU39956B (en) | 1985-06-30 |
| NZ179231A (en) | 1978-03-06 |
| FI760175A7 (OSRAM) | 1976-07-28 |
| FI62081B (fi) | 1982-07-30 |
| FI62081C (fi) | 1982-11-10 |
| ES444667A1 (es) | 1977-11-16 |
| PT64741A (fr) | 1976-02-01 |
| PH13605A (en) | 1980-08-05 |
| IL48902A (en) | 1979-10-31 |
| IE43157L (en) | 1976-07-27 |
| DK157300C (da) | 1990-05-07 |
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