Dicyclohexylcarbodiimide → N-(3-amino-5-nitrophenyl)-2,2-dimethyl-1,3-dioxolane-4-carboxamide

Participants

Reaction Steps

To a solution of 0.5 g (2.9 mmole) of 2,2-dimethyl-1,3-dioxolane-4-carboxylic acid in 2 ml of methylene chloride, at 0° C., was added a solution of 0.216 g of 3,5-diaminonitrobenzene (1.3 mmole) in 2 ml of methylene chloride and 1 ml of pyridine, followed by 0.61 g (3.0 mmole) of dicyclohexylcarbodiimide. The mixture was stirred 72 hours, diluted with ethyl acetate, filtered and the filtrate evaporated to dryness in high vacuum. The residue was chromatographed over silica gel; elution with 9:1 chloroform-ethyl acetate gave two fractions. The first fraction, 170 mg was the bis-acylated material. The second fraction was evaporated to dryness to give 250 mg of N-(3-amino-5-nitrophenyl)-2,2-dimethyl-1,3-dioxolane-4-carboxamide.

Provenance & Evidence