4-(Chloromethyl)-2-methyl-1,3-thiazole → HCID 23205613, compound

Participants

Reaction Conditions

Reaction Steps

1.5 g N,N'-bis-(3,4,5-trimethoxybenzyl) ethylenediamine dichlorhydrate were solubilized in 30 ml of a 1:1 ethanol/water mixture. The pH of the solution was brought to 11 using a soda solution. A solution of 1.25 g 4-chloromethyl-2-methylthiazole in solution in 10 ml water were added all at once. The mixture was heated for 5 hours at 45° C., while maintaining the pH at between 10 and 11 by adding a soda solution. After cooling, the ethanol was evaporated under a vacuum and the mixture was acidified to a pH of 1 using concentrated HCl. Extraction was carried out using 3×25 ml dichloromethane, then the organic phase was dried and dry-evaporation effected. The oil obtained was taken up in 10 ml ethanol +0.5 ml concentrated HCl. The resultant precipitate was filtered and washed in ethylic ether. The solid was then recrystallized in 20 ml isopropanol containing 1% water. In this way, 600 mg of a white powder having a melting point of 190° C. was obtained, whose proton NMR spectrum (400 MHZ) and ultimate analysis matched the expected structure (existing as a dichlorhydrate).

Provenance & Evidence