Triethylamine → Rac. 2-iodo-benzoic acid-(1-oxo-prop-2-yl-amide)

Participants

Reaction Steps

A solution of 54.9 g (345 mmol) of sulfur trioxide-pyridine complex in 150 ml of DMSO is added dropwise at RT to 35 g (115 mmol) of rac. 2-iodo-benzoic acid-(1-hydroxy-prop-2-yl-amide) in 50 ml of DMSO and 48 ml (345 mmol) of triethylamine. After 10 min, the mixture is poured onto 0.4 l of EtOAc, 0.2 l of sat. NaHCO3 solution and 0.2 l of water, the aqueous phase is separated and extracted 4 more times with EtOAc. The organic phases are washed with water and brine, dried (Na2SO4) and concentrated by evaporation to form rac. 2-iodo-benzoic acid-(1-oxo-prop-2-yl-amide).

Provenance & Evidence