Sodium Iodide → HCID 18961585, compound

HRID 1707546Notes

Reaction equation

HRID 1707546 reaction equation
[C:1]([O:4][CH:5](Cl)[CH3:6])(=[O:3])[CH3:2].[C:8]([NH:11][C:12]1[C:13]([I:28])=[C:14]([N:23]([C:25](=[O:27])[CH3:26])[CH3:24])[C:15]([I:22])=[C:16]([C:19]([O-:21])=[O:20])[C:17]=1[I:18])(=[O:10])[CH3:9].[K+].[I-].[Na+]>CN(C=O)C>[C:8]([NH:11][C:12]1[C:13]([I:28])=[C:14]([N:23]([C:25](=[O:27])[CH3:26])[CH3:24])[C:15]([I:22])=[C:16]([C:19]([O:21][CH:5]([O:4][C:1](=[O:3])[CH3:2])[CH3:6])=[O:20])[C:17]=1[I:18])(=[O:10])[CH3:9]

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 5218651-Chloroethyl acetateHCID 23717801potassium 5-(N-acetylamino)3-(N-acetyl-N-methylamino)-2,4,6-triiodobenzenecarboxylate

Product 1

HCID 18961585HCID 18961585, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

1-Chloroethyl acetate (Neuenschwander, Markus et. al., Helv. Chim. Acta, 61 (1978) 2047) (4.38 g, 35.7 mmol) in dry DMF (50 ml) is added dropwise at 50° C. to a solution of potassium 5-(N-acetylamino)-3-(N-acetyl-N-methylamino)-2,4,6,-triiodobenzenecarboxylate (21.64 g, 32.5 mmol) and sodium iodide (0.26 g, 1.75 mmol) in dry DMF (320 ml). The precipitate is removed by filtration after stirring for 20 hours and the solvent is removed at reduced pressure. The residue is dissolved in chloroform (300 ml) and washed four times with a saturated sodium hydrogen carbonate solution. After drying with magnesium sulfate the solution is treated with activated carbon and the solvent is removed at reduced pressure to give the title compound:

Workup

  1. customThe precipitate is removed by filtration
  2. customthe solvent is removed at reduced pressure
  3. dissolutionThe residue is dissolved in chloroform (300 ml)
  4. washwashed four times with a saturated sodium hydrogen carbonate solution
  5. dry with materialAfter drying with magnesium sulfate the solution
  6. additionis treated with activated carbon
  7. customthe solvent is removed at reduced pressure

Sources & evidence

ORD record
ord-87758eb82ea149e99dfc2377bc7290ba
Source dataset
uspto-grants-1994_10
Patent number
US05354549

Reaction notes

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