Sodium Iodide → HCID 10055828, compound

HRID 745024Notes

Reaction equation

HRID 745024 reaction equation
[C:1](=[O:9])([O:6][CH2:7][CH3:8])[O:2][CH:3](Cl)[CH3:4].[C:10]([NH:13][C:14]1[C:15]([I:30])=[C:16]([N:25]([C:27](=[O:29])[CH3:28])[CH3:26])[C:17]([I:24])=[C:18]([C:21]([O-:23])=[O:22])[C:19]=1[I:20])(=[O:12])[CH3:11].[K+].[I-].[Na+]>CN(C)C=O>[C:10]([NH:13][C:14]1[C:15]([I:30])=[C:16]([N:25]([C:27](=[O:29])[CH3:28])[CH3:26])[C:17]([I:24])=[C:18]([C:21]([O:23][CH:3]([O:2][C:1]([O:6][CH2:7][CH3:8])=[O:9])[CH3:4])=[O:22])[C:19]=1[I:20])(=[O:12])[CH3:11]

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 162095Carbonic acid, 1-chloroethyl ethyl esterHCID 23717801potassium 5-(N-acetylamino)3-(N-acetyl-N-methylamino)-2,4,6-triiodobenzenecarboxylate

Product 1

HCID 10055828HCID 10055828, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

1-Chloroethyl ethyl carbonate (10.00 g, 66.0 mmol) was added dropwise during 1.5 hour at room temperature to a solution of potassium 5-(N-acetylamino)3-(N-acetyl-N-methylamino)-2,4,6-triiodobenzenecarboxylate (40.00 g, 60.0 mmol) and sodium iodide (0.89 g, 6.0 mmol) in dry dimethylformamide (200 ml). After stirring at 50° C. for 24 hours the solvent was removed at reduced pressure. The residue was dissolved in chloroform (120 ml) and washed four times with a saturated sodium hydrogen carbonate solution and twice with water. After drying with magnesium sulfate, treatment with activated charcoal and filtration, the title compound was crystallised by concentrating the solution at reduced pressure. Yield: (79%). Purity by HPLC: 99%. 1H-NMR (DMSO-d6): delta=1.25 (t, J=7 Hz, CH3); 1.64 (d, J=6 Hz, CH3); 1.67 (s, N(Me)COCH3); 2.05(s, NCOCH3); 2.96 (s, NCH3); 4.21 (q, J=7 Hz, CH2); 6.97 (q, J=6 Hz, CH); 10.10 ppm (s, NH).

Workup

  1. customwas removed at reduced pressure
  2. dissolutionThe residue was dissolved in chloroform (120 ml)
  3. washwashed four times with a saturated sodium hydrogen carbonate solution
  4. dry with materialAfter drying with magnesium sulfate, treatment with activated charcoal and filtration
  5. customthe title compound was crystallised
  6. concentrationby concentrating the solution at reduced pressure

Sources & evidence

ORD record
ord-d28ab77b63924d79b181bf8dba6a02d9
Source dataset
uspto-grants-1996_09
Patent number
US05559266

Reaction notes

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