Ammonium Chloride → Hydrochloric Acid

Participants

Reaction Steps

A stirred mixture of 1-[2,2-bis(4-nitrobenzylthio)ethyl]-1H-imidazole (924 mg), iron powder (1.08 g) and ammonium chloride (862 mg) in water (30 ml) was refluxed for 2 hours. The cooled mixture was thoroughly extracted with CH2Cl2 and the combined CH2Cl2 extracts were washed with water and dried over Na2SO4. Removal of the CH2Cl2 left 360 mgs. of the crude amine as a viscous oil. The black residue, which resisted extraction with CH2Cl2, was extracted with dilute aqueous oxalic acid. The aqueous mixture was filtered, and the filtrate was made basic with aqueous potassium hydroxide. Extraction of the filtrate with CH2Cl2 gave another crop of the crude amine which was combined with the 360 mg. fraction. The crude amine was chromatographed on silicic acid (20 g) with CH2Cl2 /CH3OH/diethyl amine (500:25:2) to afford 340 mg. of the pure amine. Treatment of a solution of the pure base in ethanol with hydrogen chloride afforded the title compound as a light tan amorphous solid which melted indistinctly with decomposition.

Provenance & Evidence