Sodium Iodide → HCID 15572436, compound

HRID 1707547Notes

Reaction equation

HRID 1707547 reaction equation
ClC[CH2:3][C:4]([CH3:9])([CH3:8])[C:5]([O-:7])=[O:6].[C:10]([NH:13][C:14]1[C:15]([I:29])=[C:16]([C:25]([NH:27][CH3:28])=[O:26])[C:17]([I:24])=[C:18]([C:21]([O-:23])=[O:22])[C:19]=1[I:20])(=[O:12])[CH3:11].[K+].[I-].[Na+].[CH3:33]N(C=O)C>>[C:10]([NH:13][C:14]1[C:15]([I:29])=[C:16]([C:25]([NH:27][CH3:28])=[O:26])[C:17]([I:24])=[C:18]([C:21]([O:23][CH2:33][O:7][C:5](=[O:6])[C:4]([CH3:9])([CH3:8])[CH3:3])=[O:22])[C:19]=1[I:20])(=[O:12])[CH3:11]

Participants

5

Reactant 4

HCID 5238Sodium IodideHCID 6228Dimethylformamide2×HCID 217530474-Chloro-2,2-dimethylbutanoateHCID 23692363potassium 5-(N-acetylamino)-3-(methylaminocarbonyl)-2,4,6-triiodobenzenecarboxylate

Product 1

HCID 15572436HCID 15572436, compound

Procedure

Chloromethylpivalate (7.62 g, 50.6 mmol) in dry DMF (84 ml) is added dropwise at 50° C. to a solution of potassium 5-(N-acetylamino)-3-(methylaminocarbonyl)-2,4,6-triiodobenzenecarboxylate (30.00 g, 46.0 mmol) and sodium iodide (0.37 g, 2.5 mmol) in dry DMF (450 ml). The precipitate is removed by filtration after stirring for 4 hours and the solvent is removed at reduced pressure. The residue is triturated and washed repeatedly in water and finally recrystallised from isopropanol.

Workup

  1. customThe precipitate is removed by filtration
  2. customthe solvent is removed at reduced pressure
  3. customThe residue is triturated
  4. washwashed repeatedly in water
  5. customfinally recrystallised from isopropanol

Sources & evidence

ORD record
ord-9329820ca65a4b90a7ab2c9f05999998
Source dataset
uspto-grants-1994_10
Patent number
US05354549

Reaction notes

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