N,N-Diethylaniline → HCID 13339703, compound

Participants

Reaction Steps

3-Acetyloxy-4,5-diethoxyaniline (1.0 g) and N,N-diethylaniline (0.70 g) were dissolved in toluene (15 ml). To the resultant solution was dropwise added isopropyl chloroformate (0.70 g) in 5 minutes under ice-cooling. The resultant mixture was allowed to stand at room temperature for 12 hours, poured into ice-water and extracted with ethyl acetate. The extract was washed with water, dried over magnesium sulfate and concentrated under reduced pressure. The reside was purified by silica gel chromatography using a mixture of benzene and tetrahydrofuran as the eluent to give isopropyl N-(3-acetyloxy-4,5-diethoxyphenyl)carbamate (Compound No. 4) (1.21 g) in a yield of 88.9%. M.P., 108°-109° C.

Provenance & Evidence