Process for preparing substituted nitroimidazoles
AssigneeMerck & Co., Inc.
InventorsLudwig Salce, Erwin F. Schoenewaldt
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Abstract
2-(P-Fluorophenyl)-1-alkyl or 1-(2'-hydroxyalkyl)-5-nitroimidazoles are prepared by reacting a dialkoxy-carbonium salt, or a 1,3-dioxolenium salt, respectively, with 2-(p-fluorophenyl)-1-alkoxymethyl-4-nitroimidazole. The compounds prepared are useful in the control of enterohepatitis in poultry, especially in turkeys.
Claims3
A process for preparing 1-(2'-hydroxyethyl)-2-(p-fluorophenyl)-5-nitroimidazole by reacting in a solvent selected from the group consisting of 1,2-dimethoxyethane, 1,2-dichloroethane, dioxane, methylene chloride, ethyl acetate, methyl formate or 1,2-diacetoxyethane at a temperature of from -10.degree.C. to the reflux temperature of said solvent for from 15 minutes to 24 hours, each molar equivalent of a compound of the formula ##SPC5##
- with from 1 to 5 molar equivalents of a compound of the formula:
- ##EQU3## wherein X.sup.- is BF.sub.4.sup.-, SbCl.sub.6.sup.-, or SbF.sub.6.sup.-, and R is alkyl of 1-6 carbon atoms thereby forming a quaternary first intermediate;
- treating said quaternary first intermediate with ultraviolet irradiation thereby giving a second intermediate of the formula:
- ##SPC6##
- where R is as previously defined;
- and hydrolyzing the second intermediate.
A process for preparing 1-(2'-hydroxyethyl)-2-(p-fluorophenyl)-5-nitroimidazole by reacting in a solvent selected from the group consisting of 1,2-dimethoxyethane, 1,2-dichloroethane, dioxane, methylene chloride, ethyl acetate, methyl formate of 1,2-diacetoxyethane at a temperature of -10.degree.C. to the reflux temperature of said solvent for from 15 minutes to 24 hours, each molar equivalent of a compound of the formula:
- ##SPC7##
- with from 1 to 5 molar equivalents of a compound of the formula:
- ##EQU4## wherein X.sup.- is BF.sub.4.sup.-, SbCl.sub.6.sup.-, and R is alkyl of 1-6 carbon atoms, thereby forming a quaternary first intermediate;
- heating said quaternary first intermediate at a temperature of from 100.degree.C. to 300.degree.C. for from 1/2 to 5 hours thereby forming a second intermediate of the formula:
- ##SPC8##
- where R is as previously defined;
- and hydrolyzing the second intermediate.
A process of preparing 1-(2'-hydroxyethyl)-2-(p-fluorophenyl)-5-nitroimidazole by reacting in a solvent selected from the group consisting of 1,2-dimethoxyethane, 1,2-dichloroethane, dioxane, methylene chloride, ethyl acetate, methyl formate or 1,2-diacetoxyethane at a temperature of from -10.degree.C. to the reflux temperature of said solvent for from 15 minutes to 24 hours a 1-loweralkoxymethyl-2-(p-fluorophenyl)-4-nitroimidazole with a 1,3-dioxolenium salt of the formula:
- ##EQU5## thereby forming a quaternary intermediate wherein:
- X.sup.- is BF.sub.4.sup.-, SbCl.sub.6.sup.- or SbF.sub.6.sup.- and R represents an alkyl group of 1-6 carbon atoms;
- treating said quaternary intermediate with a polar nucleophile selected from the group consisting of potassium iodide, hydrogen bromide, potassium thiocyanate, potassium cyanide, triethylamine or pyridine;
- thereby forming a second intermediate:
- ##SPC9##
- wherein R is as previously defined;
- and hydrolyzing the second intermediate.
Dependencies are inferred from the claim text.