Ammonium Hydroxide → Ethyl 2-(3,5-bis(acetylamino)-2,4,6-triiodobenzoyloxy)butyrate

HRID 1108933Notes

Reaction equation

HRID 1108933 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

Reactant 3

HCID 14923Ammonium HydroxideHCID 79039Butanoic acid, 2-bromo-, ethyl esterHCID 23672589Sodium Amidotrizoate

Product 1

HCID 11377613Ethyl 2-(3,5-bis(acetylamino)-2,4,6-triiodobenzoyloxy)butyrateYield 66.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 500 mL 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 3 L 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.)

Workup

  1. temperatureThe mixture was heated on a steam bath for 20 h
  2. filtrationThe solid was filtered
  3. washwashing with water
  4. customair-dried
  5. customThe solid was further purified by crystallization from 50% aqueous ethanol (after treatment with decolorizing carbon)
  6. customaffording two crops which
  7. customwere dried at 100° C. overnight

Sources & evidence

ORD record
ord-13862ceaabd24e6fb2eb5f0e1f6e6e4e
Source dataset
uspto-grants-1994_06
Patent number
US05318768

Reaction notes

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