Benzyl Alcohol → HCID 46203576, compound

Participants

Reaction Steps

Stage B 167 mg of 3,9-dimethyl[1,3]thiazolo[3,2-a]benzimidazol-9-ium iodide (0.51 mmol) and 162 mg of NaOH (8 eq) were solubilised in benzyl alcohol (5 mL) and the solution stirred under reflux. After 48 h water was added (20 mL) and the mixture extracted with CH2Cl2 (3×20 mL). The organic layer was dried with MgSO4 and evaporated under reduced pressure. The residue was then purified by chromatography on silica gel (eluent: CH2Cl2) to afford a mixture 55/45 of 1-[(1E)-1-(benzylsulfanyl)prop-1-en-2-yl]-3-methyl-1,3-dihydro-2H-benz imidazol-2-one and 1-[(1Z)-1-(benzyl sulfanyl)prop-1-en-2-yl]-3-methyl-1,3-dihydro-2H-benzimidazol-2-one isomers as a colourless oil (127 mg, 81% overall yield). HRMS m/z calcd C18H19N2OS [M+H]+: 311.1212; found: 311.1215 (analysis on the isomer mixture). The two isomers were separated by preparative TLC (eluent: CHCl3, eluted three times).

Provenance & Evidence