Sodium Iodide → HCID 18961589, compound

HRID 1707553Notes

Reaction equation

HRID 1707553 reaction equation
[C:1]([O:4][CH:5](Cl)[CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)(=[O:3])[CH3:2].[C:14]([NH:17][C:18]1[C:19]([I:34])=[C:20]([N:29]([C:31](=[O:33])[CH3:32])[CH3:30])[C:21]([I:28])=[C:22]([C:25]([O-:27])=[O:26])[C:23]=1[I:24])(=[O:16])[CH3:15].[K+].[I-].[Na+]>CN(C=O)C>[C:14]([NH:17][C:18]1[C:19]([I:34])=[C:20]([N:29]([C:31](=[O:33])[CH3:32])[CH3:30])[C:21]([I:28])=[C:22]([C:25]([O:27][CH:5]([O:4][C:1](=[O:3])[CH3:2])[CH2:6][C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[O:26])[C:23]=1[I:24])(=[O:16])[CH3:15]

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 12398807HCID 12398807, compound2×HCID 23717801potassium 5-(N-acetylamino)3-(N-acetyl-N-methylamino)-2,4,6-triiodobenzenecarboxylate

Product 1

HCID 18961589HCID 18961589, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

1-Chloro-2-phenylethyl acetate (Intermediate 9) (4.20 g, 21.1 mmol) in dry DMF (25 ml) is added dropwise at 50° C. to a solution of potassium 5-(N-acetylamino)-3-(N-acetyl-N-methylamino)-2,4,6-triiodobenzenecarboxylate (15.5 g, 23.2 mmol) and sodium iodide (158 mg, 1.0 mmol) in dry DMF (300 ml). The precipitate is removed by filtration after stirring for 21 hours and the solvent is removed at reduced pressure. The residue is dissolved in chloroform (200 ml) and washed four times with a saturated sodium hydrogen carbonate solution. After drying with magnesium sulfate 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 (200 ml)
  4. washwashed four times with a saturated sodium hydrogen carbonate solution
  5. dry with materialAfter drying with magnesium sulfate the solvent
  6. customis removed at reduced pressure

Sources & evidence

ORD record
ord-638ec4f2f0e3469cb195d1c464d5e604
Source dataset
uspto-grants-1994_10
Patent number
US05354549

Reaction notes

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