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

HRID 1707550Notes

Reaction equation

HRID 1707550 reaction equation
[CH3:1][O:2][C:3]1[CH:13]=[CH:12][C:6]([C:7]([O:9][CH2:10]Cl)=[O:8])=[CH:5][C:4]=1[CH3:14].[C:15]([NH:18][C:19]1[C:20]([I:35])=[C:21]([N:30]([C:32](=[O:34])[CH3:33])[CH3:31])[C:22]([I:29])=[C:23]([C:26]([O-:28])=[O:27])[C:24]=1[I:25])(=[O:17])[CH3:16].[K+].[I-].[Na+]>CN(C=O)C>[C:15]([NH:18][C:19]1[C:20]([I:35])=[C:21]([N:30]([C:32](=[O:34])[CH3:33])[CH3:31])[C:22]([I:29])=[C:23]([C:26]([O:28][CH2:10][O:9][C:7](=[O:8])[C:6]2[CH:12]=[CH:13][C:3]([O:2][CH3:1])=[C:4]([CH3:14])[CH:5]=2)=[O:27])[C:24]=1[I:25])(=[O:17])[CH3:16]

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 18961586Chloromethyl 4-methoxy-3-methylbenzoate2×HCID 23717801potassium 5-(N-acetylamino)3-(N-acetyl-N-methylamino)-2,4,6-triiodobenzenecarboxylate

Product 1

HCID 189615944-Methoxy-3-methylbenzoyloxymethyl 5-(N-acetylamino)-3-(N-acetyl-N-methylamino)-2,4,6-triiodobenzenecarboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Chloromethyl 4-methoxy-3-methylbenzoate (Intermediate 8) (2.38 g, 11.0 mmol) in dry DMF (100 ml) is added dropwise at 50° C. to a solution of potassium 5-(N-acetylamino)-3-(N-acetyl-N-methylamino)-2,4,6-triiodobenzenecarboxylate (6.7 0 g, 10.0 mmol) and sodium iodide (75 mg, 0.50 mmol) in dry DMF (140 ml). The precipitate is removed by filtration after stirring for 4.5 hours and 16 hours at room temperature, and the solvent is removed at reduced pressure. The residue is dissolved in chloroform (100 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 (100 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-654bb49d07e04156b5218099e23fdf0a
Source dataset
uspto-grants-1994_10
Patent number
US05354549

Reaction notes

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