Acetonitrile → HCID 638695, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of 2.65 g (11.4 mmol) of 1,2-dimethyl-isothiourea hydroiodide and 1.00 g (10.4 mmol) of 2-bromo-3-isopropoxy-propenal 8 mL of MeCN was added 1.58 g (11.4 mmol) of K2CO3 (Shilcrat, S. C. et al. J. Org. Chem., 1997, 62, 8449–8454). The mixture was stirred at 35° C. under N2 for 16 h, water (20 ml) was added, and the mixture was extracted with CH2Cl2 (200 mL). The extract was dried over MgSO4, filtered, concentrated, and chromatographed (0 to 100% EtOAc in hexanes) to provide 1.09 g of 3-methyl-2-methylsulfanyl-3H-imidazole-4-carbaldehyde and 284 mg of 1-methyl-2-methylsulfanyl-1H-imidazole-4-carbaldehyde.

Provenance & Evidence