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

HRID 1707548Notes

Reaction equation

HRID 1707548 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([O:8][CH2:9]Cl)=[O:7].[C:11]([NH:14][C:15]1[C:16]([I:31])=[C:17]([N:26]([C:28](=[O:30])[CH3:29])[CH3:27])[C:18]([I:25])=[C:19]([C:22]([O-:24])=[O:23])[C:20]=1[I:21])(=[O:13])[CH3:12].[Cs+].[I-].[Na+]>CN(C=O)C>[C:11]([NH:14][C:15]1[C:16]([I:31])=[C:17]([N:26]([C:28](=[O:30])[CH3:29])[CH3:27])[C:18]([I:25])=[C:19]([C:22]([O:24][CH2:9][O:8][C:6]([C:2]2[S:1][CH:5]=[CH:4][CH:3]=2)=[O:7])=[O:23])[C:20]=1[I:21])(=[O:13])[CH3:12]

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 11148043Chloromethyl Thiophene-2-carboxylate2×HCID 23675689cesium 5-(N-acetylamino)-3-(N-acetyl-N-methylamino)-2,4,6-triiodobenzenecarboxylate

Product 1

HCID 18961595(2-Thienylcarbonyloxy)methyl 5-(N-acetylamino)-3-(N-acetyl-N-methylamino)-2,4,6-triiodobenzenecarboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Chloromethyl 2-thiopbenecarboxylate (0.63 g, 3.6 mmol) (Intermediate 6) in dry DMF (70 ml) is added dropwise at 50° C. to a solution of cesium 5-(N-acetylamino)-3-(N-acetyl-N-methylamino)-2,4,6-triiodobenzenecarboxylate (3.00 g, 3.9 mmol) and sodium iodide (28 mg, 0.19 mmol) in dry DMF (45 ml). The precipitate is removed by filtration after stirring for 4 hours and the solvent is removed at reduced pressure. The residue is dissolved in chloroform (50 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 (50 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-99a08d8eedec450ba4db09fa18f40e82
Source dataset
uspto-grants-1994_10
Patent number
US05354549

Reaction notes

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