Chloroacetone → HCID 13060079, compound

Participants

Reaction Steps

A mixture of 5-methyl-2-thioxo-2,3-dihydro-1H-imidazole-4-carboxylic acid ethyl ester (5.37 mmol) and chloroacetone (6.44 mmol) in EtOH (10 mL) is heated at reflux for 150 min. The solvents are removed in vacuo and a solution of POCl3 (16.1 mmol) in MeCN (10 mL) is added. The mixture is stirred at reflux for 60 h, concentrated in vacuo and diluted with chloroform. Ice water is added and the mixture is neutralized by addition of Na2CO3. The layers are separated and the aq. layer is extracted with chloroform. The combined organic layers are dried over Na2SO4 and concentrated in vacuo to give a mixture of two regioisomers (see A.7.7) which are separated by FC (heptane to heptane/EtOAc 3/7). LC-MS: tR=0.71 min; [M+H]+=225.0.

Provenance & Evidence