Ethyl Acetate → 3-Amino-5-(aminocarbonyl)-2,4,6-triiodobenzoyl chloride

HRID 2095223Notes

Reaction equation

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]

Participants

Conditions

Temperature: 74 °C

Procedure

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 %.

Workup

temperatureThe reaction mixture was maintained at 74° C. for 12 hours
temperatureWhile cooling to 45° C.
temperaturethe reaction mixture was cooled to 28° C
stirringAfter stirring for 7 hours
customthe solid product was isolated by filtration
washthe solids were washed with ethyl acetate (250 kg)
customAfter drying at 40° C. under vacuum

Sources & evidence

ORD record: ord-b0aff3c767f448c8bc7eab00e993ef2c
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08445725B2

Reaction notes

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