Acetoxyacetyl chloride → 5-Acetoxyacetamido-3-methylcarbamoyl2,4,6-triiodobenzoyl chloride

Participants

Reaction Conditions

Reaction Steps

To a slurry of (2) (170 g, 0.29 mol) in 350 ml of N,N-dimethylacetamide (DMAc) was added 4-dimethylaminopyridine (DMAP) (1.86 g, 0.015 mol). The mixture was cooled to 0° C. and acetoxyacetyl chloride (62 ml, 78.6 g, 0.58 mol) was added dropwise, keeping the temperature <5° C. The mixture was stirred at 30° C. for 16 hours. The reaction mixture containing the solid white product was immersed in an ice bath for 2 hours, filtered, stirred with cold THF (1100 ml) for 1 hour, filtered and dried under vacuum for 2 days to give 190 g of product 3 (0.30 mol, 95%) as a white solid. 13C NMR (75.5 MHz, DMSO, ref. DMSO at 39.5 ppm): 170.6, 170.2, 169.9, 166.1, 166.0, 151.7, 149.8, 143.6, 143.5, 103.4, 97.0, 88.8, 62.4, 26.0, 20.6.

Provenance & Evidence