Potassium Iodide → HCID 21712000, compound

HRID 650457Notes

Reaction equation

HRID 650457 reaction equation
[C:1](=[O:25])([O:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[O:2][CH:3](Cl)[CH3:4].[C:26]([NH:29][C:30]1[C:31]([I:46])=[C:32]([N:41]([CH3:45])[C:42](=[O:44])[CH3:43])[C:33]([I:40])=[C:34]([C:37]([O-:39])=[O:38])[C:35]=1[I:36])(=[O:28])[CH3:27].[K+].[I-].[K+]>CN(C)C=O>[C:26]([NH:29][C:30]1[C:31]([I:46])=[C:32]([N:41]([CH3:45])[C:42](=[O:44])[CH3:43])[C:33]([I:40])=[C:34]([C:37]([O:39][CH:3]([O:2][C:1]([O:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])=[O:25])[CH3:4])=[O:38])[C:35]=1[I:36])(=[O:28])[CH3:27]

Participants

5

Reactant 3

HCID 4875Potassium IodideHCID 14593424HCID 14593424, compoundHCID 23717801potassium 5-(N-acetylamino)3-(N-acetyl-N-methylamino)-2,4,6-triiodobenzenecarboxylate

Product 1

HCID 21712000HCID 21712000, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

1-Chloroethyl octadecyl carbonate (7.54 g, 20 mmol) was added at room temperature to a solution of potassium 5-acetamido-3-(N-methylacetamido)-2,4,6-triiodobenzenecarboxylate (15.99 g, 24 mmol) and potassium iodide (0.33 g, 2 mmol) in dry N,N-dimethylformamide. After stirring at 50° C. for 18 hours the solvent was removed at reduced pressure. The residue was suspended in chloroform (200 ml) and washed three times with a saturated sodium bicarbonate solution and finally twice with water. After drying with magnesium sulphate the solvent was removed at reduced pressure. Yield: 18.6 g. The product was further purified by flash chromatography (Silicagel 60, chloroform/acetonitrile 85:15). 1H NMR (DMSO-d6): δ 0.852(CH2CH3), 1.236(CH2), 1.639(CHCH3),1.657(COOCH2CH2), 1.670(N(CH3)COCH3), 2.051(NCOCH3),2.965(NCH3), 4.154(COOCH2), 6.971 (CHCH3),10.103 (NH).

Workup

  1. customwas removed at reduced pressure
  2. washwashed three times with a saturated sodium bicarbonate solution
  3. dry with materialAfter drying with magnesium sulphate the solvent
  4. customwas removed at reduced pressure
  5. customThe product was further purified by flash chromatography (Silicagel 60, chloroform/acetonitrile 85:15)

Sources & evidence

ORD record
ord-341ad26b3aae49799243addef0ca3d96
Source dataset
uspto-grants-2001_08
Patent number
US06274120B1

Reaction notes

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