C(OCC)(=O)C.[NH2:7][C:8]1[C:9]([I:22])=[C:10]([C:14]([I:21])=[C:15]([C:18]([NH2:20])=[O:19])[C:16]=1[I:17])[C:11](O)=[O:12].S(Cl)([Cl:25])=O>CN(C)C(=O)N(C)C.O>[NH2:7][C:8]1[C:9]([I:22])=[C:10]([C:14]([I:21])=[C:15]([C:18]([NH2:20])=[O:19])[C:16]=1[I:17])[C:11]([Cl:25])=[O:12]
A 4000 L glass-lined reactor was charged with ethyl acetate (2250 kg), 3-amino-5-(aminocarbonyl)-2,4,6-triiodobenzoic acid (1125 kg) and tetramethylurea (4.75 kg). The reaction mixture was stirred and heated to 74° C. Thionyl chloride (528 kg) was charged over 1 hour. The reaction mixture was maintained at 74° C. for 12 hours. While cooling to 45° C., additional ethyl acetate (180 kg) was charged. Water (73 kg) was charged over 1 hour and the reaction mixture was cooled to 28° C. After stirring for 7 hours, the solid product was isolated by filtration and the solids were washed with ethyl acetate (250 kg). After drying at 40° C. under vacuum, 927 kg of 3-amino-5-(aminocarbonyl)-2,4,6-triiodobenzoyl chloride were isolated which had a chromatographic purity of 92.4 area %.
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