Ammonium Hydroxide → Ethyl 2-(3,5-bis(acetylamino)-2,4,6-triiodobenzoyloxy)butyrate
Reaction equation
[CH3:1][C:2]([NH:4][C:5]1[C:10]([I:11])=[C:9]([NH:12][C:13]([CH3:15])=[O:14])[C:8]([I:16])=[C:7]([C:17]([O-:19])=[O:18])[C:6]=1[I:20])=[O:3].[Na+].Br[CH:23]([CH2:29][CH3:30])[C:24]([O:26][CH2:27][CH3:28])=[O:25].[OH-].[NH4+]>CN(C)C=O>[C:13]([NH:12][C:9]1[C:8]([I:16])=[C:7]([C:6]([I:20])=[C:5]([NH:4][C:2](=[O:3])[CH3:1])[C:10]=1[I:11])[C:17]([O:19][CH:23]([CH2:29][CH3:30])[C:24]([O:26][CH2:27][CH3:28])=[O:25])=[O:18])(=[O:14])[CH3:15]Participants
5
Procedure
To 500mL of dry N,N-dimethylformamide was added 159 g (0.250 mol) sodium diatrizoate and 54.5 g (0.280 mol) of ethyl 2-bromobutyrate. The mixture was heated on a steam bath for 20 h, cooled to room temperature and poured into 3L of dilute ammonium hydroxide. The solid was filtered, washing with water, and air-dried. The solid was further purified by crystallization from 50% aqueous ethanol (after treatment with decolorizing carbon) affording two crops which were dried at 100° C. overnight to afford 121 g (66%) of a white powder, m.p. 288°-290 ° C. (dec.). Analysis for C17H19I3N2O6 : Calculated/Found: C,28.05/28.36/H,2.63/2.55;I,52.3/52.3
Workup
- temperatureThe mixture was heated on a steam bath for 20 h
- filtrationThe solid was filtered
- washwashing with water
- customair-dried
- customThe solid was further purified by crystallization from 50% aqueous ethanol (after treatment with decolorizing carbon)
- customaffording two crops which
- customwere dried at 100° C. overnight
Sources & evidence
- ORD record
- ord-7c727e3c88b54dcaabd5102ae0471560
- Source dataset
- uspto-grants-1994_11
- Patent number
- US05368837
Reaction notes
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