CA1079738A - Process for the manufacture of 1-alkyl-2-(phenoxymethyl)-5-nitroimidazoles - Google Patents
Process for the manufacture of 1-alkyl-2-(phenoxymethyl)-5-nitroimidazolesInfo
- Publication number
- CA1079738A CA1079738A CA272,551A CA272551A CA1079738A CA 1079738 A CA1079738 A CA 1079738A CA 272551 A CA272551 A CA 272551A CA 1079738 A CA1079738 A CA 1079738A
- Authority
- CA
- Canada
- Prior art keywords
- methyl
- nitro
- phenoxymethyl
- imidazole
- oxidation
- 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 abstract description 12
- 230000008569 process Effects 0.000 title claims abstract description 12
- 238000004519 manufacturing process Methods 0.000 title abstract description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 17
- 229910052736 halogen Chemical group 0.000 claims abstract description 7
- 150000002367 halogens Chemical group 0.000 claims abstract description 7
- 150000002431 hydrogen Chemical group 0.000 claims abstract description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 7
- 239000001257 hydrogen Substances 0.000 claims abstract description 7
- 125000006125 ethylsulfonyl group Chemical group 0.000 claims abstract description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 4
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 4
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims abstract description 3
- BJNXOHUHVWNFLQ-UHFFFAOYSA-N 1-methyl-5-nitro-2-(phenoxymethyl)imidazole Chemical class C1=C([N+]([O-])=O)N(C)C(COC=2C=CC=CC=2)=N1 BJNXOHUHVWNFLQ-UHFFFAOYSA-N 0.000 claims abstract 2
- 125000004434 sulfur atom Chemical group 0.000 claims abstract 2
- 238000007254 oxidation reaction Methods 0.000 claims description 18
- 230000003647 oxidation Effects 0.000 claims description 16
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 8
- XTEGARKTQYYJKE-UHFFFAOYSA-M Chlorate Chemical class [O-]Cl(=O)=O XTEGARKTQYYJKE-UHFFFAOYSA-M 0.000 claims description 3
- ULQQGOGMQRGFFR-UHFFFAOYSA-N 2-chlorobenzenecarboperoxoic acid Chemical class OOC(=O)C1=CC=CC=C1Cl ULQQGOGMQRGFFR-UHFFFAOYSA-N 0.000 claims description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 claims description 2
- KRVSOGSZCMJSLX-UHFFFAOYSA-L chromic acid Substances O[Cr](O)(=O)=O KRVSOGSZCMJSLX-UHFFFAOYSA-L 0.000 claims description 2
- AWJWCTOOIBYHON-UHFFFAOYSA-N furo[3,4-b]pyrazine-5,7-dione Chemical compound C1=CN=C2C(=O)OC(=O)C2=N1 AWJWCTOOIBYHON-UHFFFAOYSA-N 0.000 claims description 2
- WQYVRQLZKVEZGA-UHFFFAOYSA-N hypochlorite Chemical class Cl[O-] WQYVRQLZKVEZGA-UHFFFAOYSA-N 0.000 claims description 2
- 229910017604 nitric acid Inorganic materials 0.000 claims description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical class OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 claims description 2
- KHIWWQKSHDUIBK-UHFFFAOYSA-N periodic acid Chemical class OI(=O)(=O)=O KHIWWQKSHDUIBK-UHFFFAOYSA-N 0.000 claims description 2
- 239000011593 sulfur Substances 0.000 claims description 2
- 239000007800 oxidant agent Substances 0.000 claims 4
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 claims 2
- 125000003375 sulfoxide group Chemical group 0.000 claims 2
- XYPISWUKQGWYGX-UHFFFAOYSA-N 2,2,2-trifluoroethaneperoxoic acid Chemical compound OOC(=O)C(F)(F)F XYPISWUKQGWYGX-UHFFFAOYSA-N 0.000 claims 1
- 239000002270 dispersing agent Substances 0.000 claims 1
- 239000012442 inert solvent Substances 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 description 7
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 239000000460 chlorine Chemical group 0.000 description 3
- 229940060038 chlorine Drugs 0.000 description 3
- 235000017168 chlorine Nutrition 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 229960002163 hydrogen peroxide Drugs 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- YZEUHQHUFTYLPH-UHFFFAOYSA-N 2-nitroimidazole Chemical compound [O-][N+](=O)C1=NC=CN1 YZEUHQHUFTYLPH-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-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
- 238000013019 agitation Methods 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Chemical group 0.000 description 2
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- -1 nitro, cyano, methylsulfonyl Chemical group 0.000 description 2
- 239000000825 pharmaceutical preparation Substances 0.000 description 2
- 229940127557 pharmaceutical product Drugs 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 2
- OVZMTYNMHXCVSY-UHFFFAOYSA-N 1-methyl-2-[(3-methyl-4-methylsulfonylphenoxy)methyl]-5-nitroimidazole Chemical compound C1=C(S(C)(=O)=O)C(C)=CC(OCC=2N(C(=CN=2)[N+]([O-])=O)C)=C1 OVZMTYNMHXCVSY-UHFFFAOYSA-N 0.000 description 1
- MRLSLMCEWBURMB-UHFFFAOYSA-N 1-methyl-2-[(4-methylphenyl)sulfanylmethyl]-5-nitroimidazole Chemical compound CN1C(=NC=C1[N+](=O)[O-])CSC1=CC=C(C=C1)C MRLSLMCEWBURMB-UHFFFAOYSA-N 0.000 description 1
- HBDLZYHJBXDDJM-UHFFFAOYSA-N 1-methyl-2-[(4-methylsulfinylphenoxy)methyl]-5-nitroimidazole Chemical compound C1=C([N+]([O-])=O)N(C)C(COC=2C=CC(=CC=2)S(C)=O)=N1 HBDLZYHJBXDDJM-UHFFFAOYSA-N 0.000 description 1
- MAGYJBIKZXSGHF-UHFFFAOYSA-N 2-[(4-ethyl-3-methylphenyl)sulfanylmethyl]-1-methyl-5-nitroimidazole Chemical compound CN1C(=NC=C1[N+](=O)[O-])CSC1=CC(=C(C=C1)CC)C MAGYJBIKZXSGHF-UHFFFAOYSA-N 0.000 description 1
- ONSXEHLVPFRVIW-UHFFFAOYSA-N 2-[(4-ethylphenyl)sulfanylmethyl]-1-methyl-5-nitroimidazole Chemical compound CN1C(=NC=C1[N+](=O)[O-])CSC1=CC=C(C=C1)CC ONSXEHLVPFRVIW-UHFFFAOYSA-N 0.000 description 1
- GXTVOQVRERBPSB-UHFFFAOYSA-N 2-[(4-ethylsulfinylphenoxy)methyl]-1-methyl-5-nitroimidazole Chemical compound C1=CC(S(=O)CC)=CC=C1OCC1=NC=C([N+]([O-])=O)N1C GXTVOQVRERBPSB-UHFFFAOYSA-N 0.000 description 1
- WKUBINCNXYCVEG-UHFFFAOYSA-N 2-[(4-ethylsulfonyl-3-methylphenoxy)methyl]-1-methyl-5-nitroimidazole Chemical compound CN1C(=NC=C1[N+](=O)[O-])COC1=CC(=C(C=C1)S(=O)(=O)CC)C WKUBINCNXYCVEG-UHFFFAOYSA-N 0.000 description 1
- VMKYTRPNOVFCGZ-UHFFFAOYSA-N 2-sulfanylphenol Chemical compound OC1=CC=CC=C1S VMKYTRPNOVFCGZ-UHFFFAOYSA-N 0.000 description 1
- YNJSNEKCXVFDKW-UHFFFAOYSA-N 3-(5-amino-1h-indol-3-yl)-2-azaniumylpropanoate Chemical compound C1=C(N)C=C2C(CC(N)C(O)=O)=CNC2=C1 YNJSNEKCXVFDKW-UHFFFAOYSA-N 0.000 description 1
- GLGRLYGELVHLDM-UHFFFAOYSA-N 5-nitro-2-(phenoxymethyl)-1h-imidazole Chemical compound N1C([N+](=O)[O-])=CN=C1COC1=CC=CC=C1 GLGRLYGELVHLDM-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 238000007689 inspection Methods 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 150000004965 peroxy acids Chemical class 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000002226 simultaneous effect Effects 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 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
- C07D233/66—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 hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/91—Nitro radicals
- C07D233/92—Nitro radicals attached in position 4 or 5
- C07D233/94—Nitro radicals attached in position 4 or 5 with hydrocarbon radicals, substituted by oxygen or sulfur atoms, attached to other ring members
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Preventing Corrosion Or Incrustation Of Metals (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19762607789 DE2607789A1 (de) | 1974-12-16 | 1976-02-26 | Verfahren zur herstellung von 1-methyl-2-(alkylsulfonyl)-phenoxy-methyl)- 5-nitro-imidazolen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1079738A true CA1079738A (en) | 1980-06-17 |
Family
ID=5970911
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA272,551A Expired CA1079738A (en) | 1976-02-26 | 1977-02-24 | Process for the manufacture of 1-alkyl-2-(phenoxymethyl)-5-nitroimidazoles |
Country Status (12)
| Country | Link |
|---|---|
| AT (1) | AT361468B (en:Method) |
| CA (1) | CA1079738A (en:Method) |
| CH (1) | CH624942A5 (en:Method) |
| DK (1) | DK144524C (en:Method) |
| EG (1) | EG13828A (en:Method) |
| ES (1) | ES456117A2 (en:Method) |
| FI (1) | FI770599A7 (en:Method) |
| IT (1) | IT1115608B (en:Method) |
| LU (1) | LU76834A1 (en:Method) |
| NL (1) | NL7701838A (en:Method) |
| NO (1) | NO770648L (en:Method) |
| SE (1) | SE7702126L (en:Method) |
-
1977
- 1977-02-21 ES ES456117A patent/ES456117A2/es not_active Expired
- 1977-02-21 NL NL7701838A patent/NL7701838A/xx not_active Application Discontinuation
- 1977-02-23 EG EG111/77A patent/EG13828A/xx active
- 1977-02-24 CH CH231377A patent/CH624942A5/de not_active IP Right Cessation
- 1977-02-24 IT IT20658/77A patent/IT1115608B/it active
- 1977-02-24 CA CA272,551A patent/CA1079738A/en not_active Expired
- 1977-02-24 FI FI770599A patent/FI770599A7/fi not_active Application Discontinuation
- 1977-02-24 LU LU76834A patent/LU76834A1/xx unknown
- 1977-02-25 AT AT128477A patent/AT361468B/de not_active IP Right Cessation
- 1977-02-25 NO NO770648A patent/NO770648L/no unknown
- 1977-02-25 DK DK84177A patent/DK144524C/da not_active IP Right Cessation
- 1977-02-25 SE SE7702126A patent/SE7702126L/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ES456117A2 (es) | 1978-03-01 |
| IT1115608B (it) | 1986-02-03 |
| DK144524C (da) | 1982-09-06 |
| SE7702126L (sv) | 1977-08-27 |
| NO770648L (no) | 1977-08-29 |
| DK144524B (da) | 1982-03-22 |
| FI770599A7 (en:Method) | 1977-08-27 |
| CH624942A5 (en) | 1981-08-31 |
| NL7701838A (nl) | 1977-08-30 |
| AT361468B (de) | 1981-03-10 |
| ATA128477A (de) | 1980-08-15 |
| LU76834A1 (en:Method) | 1977-09-26 |
| DK84177A (da) | 1977-08-27 |
| EG13828A (en) | 1982-09-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |