Methylamine → Ranisen

Participants

Reaction Conditions

Reaction Steps

Combine 2-nitromethylene-thiazolidine (146 g, 1.0 mol) and acetonitrile (250 mL). Heat to 40° C. Add methylamine (90 g). After 30 minutes, cool to about -10° C. Add a solution of 5-[(dimethylamino)methyl]-2-(chloromethyl)-furan hydrochloride as obtained in Example 3.1, maintained at 50° C. to 60° C. to prevent crystallization (about 322 g of solution over 3 hours). Add methylamine (120 g). Warm to 40° C. while adding methylamine (65 g). After 30 minutes, cool to 0° C. Add the remainder of the solution of 5-[(dimethylamino)methyl]-2-(chloromethyl)-furan hydrochloride. After the addition is complete, evaporate in vacuo to give a residue. Partition the residue between methyl isobutyl ketone and aqueous 10% potassium carbonate solution. Separate the layers and extract the aqueous layer with methyl isobutyl ketone. Combine the organic layers extract with water. Evaporate the organic layer in vacuo to give a residue. Recrystallize the residue from methyl isobutyl ketone to give the title compound.

Provenance & Evidence