Dimethyl Sulfate → Acetamide, N-(4-bromo-9,10-dihydro-9,10-dioxo-1-anthracenyl)-N-methyl-

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-bromo-1-acetylaminoanthraquinone (purity 98%, 35.1 g), monochlorobenzene (420 g), tetra-n-butyl ammonium bromide (0.3 g) and 96% potassium hydroxide (12.0 g) was stirred for one hour while being maintained at 30° C. Dimethylsulfuric acid (25.2 g) was dropped at 30° C. over 2 hours. The mixture was stirred at 30° C. for 30 minutes, 40° C. for 2 hours and 50° C. for 4 hours, successively. After water (200 g) was added, the solution was stirred for 1 hour while being maintained at 50° C. pH of the aqueous phase was 10 or higher. After acetic acid (0.5 g) was added for neutralization (pH of the aqueous phase being 7), monochlorobenzene was recovered by heating. After being cooled down to 50° C., the solution was filtered. A solid material was washed and dried to obtain 4-bromo-N-acetyl-1-methylaminoanthraquinone (35.0 g, purity 94.0%, yield 91.9%).

Provenance & Evidence