2,4-Dichlorobenzoic Acid → HCID 86646333, compound

Participants

Reaction Steps

1,1′-Carbonyl-diimidazole (4.22 g, 26 mmol) was added to a solution of 2,4-dichlorobenzoic acid (4.73 g, 24.8 mmol) in 100 ml dichloromethane the mixture was stirred for 30 minutes at room temperature and subsequently refluxed for 30 minutes. Then 6-chloro-pyridine-3-sulfonic acid amide (5.00 g, 26 mmol) and 1,8-diazabicylo[5.4.0]undec-7-en (3.96 g, 26 mmol) were added and the mixture was stirred at room temperature overnight. After evaporation to dryness the residue was taken up with 100 ml ethyl acetate and washed with 1 M HCl and 1 M NaOH and the organic phase was dried over sodium sulphate and concentrated in vacuo. Flash chromatography (SiO2, heptane-ethyl acetate gradient) yielded 6.72 g of the title compound as a white solid, m/z=365 (ES+), 363 (ES−).

Provenance & Evidence