Methyl iodide → HCID 13421472, compound

Participants

Reaction Steps

Isopropyl N-(3-nitro-4,5-diethoxyphenyl)carbamate (3.12 g) and iodomethane (4.30 g) were dissolved in tetrahydrofuran (10 ml). The resultant solution was dropwise added to a tetrahydrofuran solution containing potassium hydroxide (1.68 g) and tetra-n-butylammonium bromide (1.0 g). After being allowed to stand at room temperature for 12 hours, the reaction mixture was poured into ice-water and extracted with toluene. 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 toluene and ethyl acetate as the eluent to give isopropyl N-methyl-N-(3-nitro-4,5-diethoxyphenyl)carbamate (Compound No. 161) (2.92 g) in a yield of 89.5%. nD20.0 1.5075.

Provenance & Evidence