Methylamine → HCID 178485068, compound

Participants

Reaction Conditions

Reaction Steps

N-cyano-N'-{2-[(5-methylimidazol-4-yl)-methylthio]-ethyl}-S-methylisothiourea monohydrate (14.35 g; 0.05 mole) is suspended in distilled water (50 ml), stirred and heated. At a bath temperature of 50° C., aqueous methylamine solution (18.5 ml containing 411 g/liter of methylamine, i.e. 0.245 mole equal to 4.9 equivalents) is added. The evolving gas is led to an equipment for destruction (annihilation). The reaction mixture is kept in a bath of 50°-55° C. for 2.5 hours. Initially, the mixture becomes considerably thinner, then, in most cases, N-methyl-N'-{2-[(5-methylimidazol-4-yl)-methylthio]-ethyl}-N"-cyanoguanidine begins to precipitate without appearing of a complete solution. The mixture becomes thicker and eventually the stirring is stopped. After 2.5 hours the mixture is rapidly heated to 90° C. and stirred at this temperature for 30 minutes. The solution should not contain undissolved material. The solution is poured without cooling onto stirred ice (70 g). A clear solution of 0° to 10° C. is formed which becomes turbid and granular, and well-settling crystals separate. The solution is kept in a refrigerator for 2 hours, then filtered and washed with distilled water (2×10 ml). The wet weight of this precipitate is 14.8 g. After drying at 40° C., the dry weight of N-methyl-N'-{2-[(5-methylimidazol-4-yl)-methylthio]-ethyl}-N"-cyanoguanidine H is 12.27 g (90.82%); m.p. 73°-75° C.

Provenance & Evidence