Sodium Iodide → Acetyloxvmethyl 5-(N-acetylamino)-3-(N-acetyl-N-methylamino)-2,4,6-triiodobenzenecarboxylate

HRID 1707551Notes

Reaction equation

HRID 1707551 reaction equation
Cl[CH2:2][O:3][C:4](=[O:6])[CH3:5].[C:7]([NH:10][C:11]1[C:12]([I:27])=[C:13]([N:22]([C:24](=[O:26])[CH3:25])[CH3:23])[C:14]([I:21])=[C:15]([C:18]([O-:20])=[O:19])[C:16]=1[I:17])(=[O:9])[CH3:8].[Cs+].[I-].[Na+]>CN(C=O)C>[C:7]([NH:10][C:11]1[C:12]([I:27])=[C:13]([N:22]([C:24](=[O:26])[CH3:25])[CH3:23])[C:14]([I:21])=[C:15]([C:18]([O:20][CH2:2][O:3][C:4](=[O:6])[CH3:5])=[O:19])[C:16]=1[I:17])(=[O:9])[CH3:8]

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 69366Chloromethyl acetateHCID 23675689cesium 5-(N-acetylamino)-3-(N-acetyl-N-methylamino)-2,4,6-triiodobenzenecarboxylate

Product 1

HCID 17807105Acetyloxvmethyl 5-(N-acetylamino)-3-(N-acetyl-N-methylamino)-2,4,6-triiodobenzenecarboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Chloromethylacetate (Neuenschwander, Markus et. al., Helv. Chim. Acta, 61 (1978) 2047) (2.30 g, 21.2 mmol) in dry DMF (100 ml) is added dropwise at 50° C. to a solution of cesium 5-(N-acetylamino)-3-(N-acetyl-N-methylamino)-2,4,6-triiodobenzenecarboxylate (13.4 g, 17.7 mmol) and sodium iodide (133 mg, 0.89 mmol) in dry DMF (210 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-74a2d873e5874faf8c6840a825c9ea64
Source dataset
uspto-grants-1994_10
Patent number
US05354549

Reaction notes

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