1-methyl-1H-imidazole-5-carbaldehyde → (NE,R)-2-methyl-N-[(3-methylimidazol-4-yl)methylidene]propane-2-sulfinamide

Participants

Reaction Steps

A solution of 1-methyl-1H-imidazole-5-carbaldehyde (1.46 g, 13.26 mmol), (R)-2-methylpropane-2-sulfinamide (2.893 g, 23.87 mmol), and tetraethoxytitanium (10.89 g, 47.73 mmol) in THF (100 mL) was heated to 65° C. for 12 h. The reaction was cooled and poured onto water. The solids were filtered off, and the filtrate was extracted with EtOAc. The layers were separated, and the organic layer was concentrated. The resulting residue was purified by SiO2 eluting with a DCM/MeOH gradient (1.5 to 2% MeOH) to afford 1.444 g (51.1%) of (R,E)-2-methyl-N-((1-methyl-1H-imidazol-5-yl)methylene)propane-2-sulfinamide (128).

Provenance & Evidence