4-Chloropyridine-2-carbaldehyde → (NE,S)-N-[(4-chloro-2-pyridinyl)methylidene]-2-methylpropane-2-sulfinamide

Participants

Reaction Steps

Liu, G. et al., J. Org. Chem., 64:1278 (1999). To a solution of S-(−)-t-butyl-sulfinamide (0.856 g, 7.06 mmol) in dichloromethane (14.13 mL) was added sequentially copper(II) sulfate (2.481 g, 15.54 mmol) and 4-chloropicolinaldehyde[1.0 g, 7.06 mmol, prepared according to a modified described by Negi etc, Synthesis, 991 (1996)]. The white suspension was stirred at rt. After 3 h, the brown suspension was filtered through CELITE®, eluting with DCM, to give a clear brown filtrate. Concentration gave a brown oil weighing 1.85 g. Purification by normal phase chromatography gave 1.31 g of 45A as a clear, yellow oil. MS (ESI) m/z: 245.0 (M+H)+.

Provenance & Evidence