Sodium Hydroxide → HCID 178440163, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 35.8 g of 5-hydroxymethyl-4-iodo-2-n-propylimidazole in 325 mL of glacial acetic acid at 20° C. was added dropwise over 1 h 290 mL of 1.0N aqueous ceric ammonium nitrate solution. The resulting mixture was stirred at 20° C. for 1 h. The reaction mixture then was diluted with water, adjusted to pH 5-6 employing aqueous sodium hydroxide solution, and extracted with chloroform. The combined organic phases were washed with water and brine, dried over anhydrous sodium sulfate, filtered, and concentrated. The resulting crude solid was recrystallized from 1-chlorobutane to furnish 29.9 g of product as a light yellow solid; mp 141°-142° C. NMR (CDCl3) δ 11.51 (br s, 1H); 9.43 (s, 1H); 2.81 (t, 2H); 1.81 (sext. 2H); 0.97 (t, 3H). ##STR74##

Provenance & Evidence