Acetate → HCID 59824358, compound

HRID 1645493Notes

Reaction equation

HRID 1645493 reaction equation
[C:1]([OH:4])(=[O:3])[CH3:2].[C:5]([OH:8])(=[O:7])[CH3:6].[C:9](O)(=O)[CH3:10].[O:13]=[C:14](Cl)[C@H:15]([C@@H:17](CO)O)O.[NH2:22][C:23]1[C:24]([I:37])=[C:25]([C:34](Cl)=[O:35])[C:26]([I:33])=[C:27]([C:31]=1[I:32])[C:28]([Cl:30])=[O:29].C([O-])(=O)C.C[C:43]([N:45](C)C)=O>>[C:1]([O:4][CH:15]([C:14](=[O:13])[NH:22][C:23]1[C:31]([I:32])=[C:27]([C:28]([Cl:30])=[O:29])[C:26]([I:33])=[C:25]([C:34](=[O:35])[NH:45][CH2:43][CH:9]=[CH2:10])[C:24]=1[I:37])[CH2:17][O:7][C:5](=[O:8])[CH3:6])(=[O:3])[CH3:2]

Participants

5

Reactant 4

HCID 175AcetateHCID 31374Dimethylacetamide2×HCID 98948585-Amino-2,4,6-triiodoisophthaloyl dichlorideHCID 131729479HCID 131729479, compound

Product 1

HCID 59824358HCID 59824358, compoundYield 90%

Procedure

In dry three necked round bottom flask fitted with an additional funnel was poured 5 amino 2, 4, 6 triiodo isophthalic 3 ally amide (7) (10 g, 0.016 mol) and 10 ml of DMAC. To the stirred and cooled solution 1, 3 acetate 4 carbonyl chloride 2, 2 dimethyl (15) (6.8 g, 0.032 mol) in 10 ml of DMAc was added dropwise over 15-20 minutes. The reaction was allowed to react 20 hours with a gentle flow of nitrogen bubbling through the reaction. The solvent was concentrated under vacuo and the resulting dark brown crude mixture was purified via normal phase column chromatography eluting with ethyl acetate and petroleum ether. After purification 11 g of an off-white solid was obtained (90% yield and 98% HPLC purity)

Workup

  1. customIn dry three necked round bottom flask
  2. customfitted with an additional funnel
  3. additionwas added dropwise over 15-20 minutes
  4. customto react 20 hours with a gentle flow of nitrogen bubbling through the reaction
  5. concentrationThe solvent was concentrated under vacuo
  6. customthe resulting dark brown crude mixture was purified via normal phase column chromatography
  7. washeluting with ethyl acetate and petroleum ether
  8. customAfter purification 11 g of an off-white solid
  9. customwas obtained (90% yield and 98% HPLC purity)

Sources & evidence

ORD record
ord-3e7eb5b775304cbba6e97c3f7194cd93
Source dataset
uspto-grants-2012_02
Patent number
US08124806B2

Reaction notes

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