Ethyl Acetate → HCID 57583233, compound

HRID 1645496Notes

Reaction equation

HRID 1645496 reaction equation
[CH3:1][N:2]([CH2:18][CH:19]=[CH2:20])[C:3](=[O:17])[C:4]1[C:12]([I:13])=[C:11]([NH2:14])[C:10]([I:15])=[C:6]([C:7]([OH:9])=O)[C:5]=1[I:16].[C:21]([OH:24])(=[O:23])[CH3:22].[C:25]([OH:28])(=[O:27])[CH3:26].[C:29]([OH:32])(=O)[CH3:30].O=C([Cl:41])[C@H]([C@@H](CO)O)O.[C:42]([O:45][CH2:46][CH3:47])(=[O:44])[CH3:43]>CC(N(C)C)=O>[C:21]([O:24][CH:47]([CH2:46][O:45][C:42](=[O:44])[CH3:43])[CH:30]([O:27][C:25](=[O:28])[CH3:26])[C:29](=[O:32])[NH:14][C:11]1[C:10]([I:15])=[C:6]([C:7]([Cl:41])=[O:9])[C:5]([I:16])=[C:4]([C:3](=[O:17])[N:2]([CH2:18][CH:19]=[CH2:20])[CH3:1])[C:12]=1[I:13])(=[O:23])[CH3:22]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 86627978HCID 86627978, compoundHCID 131729479HCID 131729479, compound

Product 1

HCID 57583233HCID 57583233, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

5-amino-2,4,6-triiodoisophathalic mono-N-methyl allylamide (8) (13.5 g, 0.0214 mol) and threonic acid chloride triacetate (18) (11.1 g, 0.0395 mol) were dissolved in dry dimethylacetamide (60 mL) and stirred for 48 hours at room temperature. The reaction mixture was diluted with ethyl acetate (250 mL) and washed with ice-water/brine (50:50, 5×25 mL). The organics were collected and dried over MgSO4, filtered and evaporated to dryness to give a brown oil. It was purified by column chromatography, eluting with petrol: ethyl acetate (10-100%, 12 column volumes, SiO2, 330 g) to give the desired product as an off white solid (10.1 g, 54%).

Workup

  1. washwashed with ice-water/brine (50:50, 5×25 mL)
  2. customThe organics were collected
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customevaporated to dryness
  6. customto give a brown oil
  7. customIt was purified by column chromatography
  8. washeluting with petrol

Sources & evidence

ORD record
ord-5244d27edb424a64965e133eb67b5a93
Source dataset
uspto-grants-2012_02
Patent number
US08124806B2

Reaction notes

Loading…