Claims
- 1. 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.
- 2. 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.
- 3. 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.
RELATED CASES
This application is a continuation of U.S. Ser. No. 286,638, filed Sept. 6, 1972, now abandoned, which in turn is a continuation-in-part of U.S. Ser. No. 40,449, filed May 25, 1970, now abandoned.
Non-Patent Literature Citations (2)
Entry |
beringer et al. J. Org. Chem. 1967, Vol. 32, pp. 2630-2632. |
Meerwein et al. Liebigs Ann. Chem. 1060, Vol. 632, pp. 38-55. |
Continuations (1)
|
Number |
Date |
Country |
Parent |
286638 |
Sep 1972 |
|
Continuation in Parts (1)
|
Number |
Date |
Country |
Parent |
40449 |
May 1970 |
|