Triethylamine → HCID 178495980, compound

Participants

Reaction Steps

A solution of acetoxyacetyl chloride (1.08 g) in dichloromethane (10 ml) was added slowly to a suspension of 4-(3-aminomethylphenyl)-2-[[(amino)(2-methoxyethyl-amino)methylene]amino] thiazole dihydrochloride (2.5 g) and triethylamine (1.60 g) in dichloromethane (40 ml) with cooling on an ice bath. The mixture was stirred at room temperature for 1 day. The solvent was removed under reduced pressure. The residue was suspended in water (100 ml). The mixture was alkalified with an aqueous potassium carbonate solution and then extracted with a mixture of ethyl acetate (250 ml) and tetrahydrofuran (50 ml). The extract was dried with magnesium sulfate and then was evaporated in vacuo. The residue was chromatographed on a silica gel column eluting with a mixture of chloroform and methanol (20:1). The solvent was removed under reduced pressure. The residue was dissolved in methanolic ammonia (50 ml). The mixture was stirred with cooling on an ice-water bath for 1 hour. The solvent was removed under reduced pressure. The residue was dissolved in ethanol (50 ml) and 4N- dioxane solution of hydrogen chloride (10 ml) was added to the mixture. The mixture was stirred at room temperature for 4 hours. The resulting precipitate was collected by filtration. Recrystallization from ethanol afforded 2-[[(amino)(2-methoxyethylamino)methylene]amino]-4-(3-hydroxyacetamidomethylphenyl)thiazole hydrochloride (0.57 g).

Provenance & Evidence