Dimethylformamide → HCID 12069418, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of sodium thiomethoxide (1.47 g) in anhydrous tetrahydrofuran (50 ml) was added dropwise a solution of N-(2-nitro-5-chlorophenyl)-N-methylcarbamic acid t-butyl ester (6.0 g) in anhydrous tetrahydrofuran (120 ml) while cooling at 0° C. The resulting mixture was stirred at 0° C. for 30 minutes and at room temperature for 1 hour. At the end of this time anhydrous DMF (30 ml) was added and the resulting mixture stirred at room temperature for 1 hour. DMF (20 ml) was added and then sodium thiomethoxide (0.73 g) and further DMF (50 ml) were added. The resulting mixture was stirred at room temperature for 7 hours. The reaction mixture was concentrated in vacuo and the residue was partitioned between ethyl acetate and aqueous sodium hydrogencarbonate solution. The extract was washed with saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate and concentrated to afford the desired compound (6.15 g).

Provenance & Evidence