Acetone → Methyl N-[4-(benzothiazol-2-ylmethoxy)-2-methylphenyl]-N-hydroxymethylcarbamate

Participants

Reaction Conditions

Reaction Steps

A mixture of 130 ml of acetone and 0.5 ml of water was added to a mixture of 10.01 g of methyl N-[4-(benzothiazol-2-ylmethoxy)-2-methylphenyl]carbamate (prepared as described in Example 21(c) below) and 5.0 g of paraformaldehyde at room temperature. 0.30 g of potassium carbonate were added to the resulting mixture and the mixture was then stirred for 12 hours at 30° C. while subjected to ultrasonic irradiation. At the end of this time the reaction mixture was filtered and the solvent was removed from the filtrate by evaporation under reduced pressure to give a residue which was purified by column chromatography through silica gel, using a gradient of dichloromethane and acetone as the eluent, gradually changing from a 9:1 by volume mixture of dichloromethane and acetone to a final 4:1 by volume mixture, to give 8.02 g (yield 73.4%) of the title compound as a solid having a melting point of 121°-123° C.

Provenance & Evidence