5-Amino-2,4,6-triiodoisophthaloyl dichloride → 2,4,6-triiodo-5-(((2-(1-methylethyl)-1,3-dioxan-5-yl)carbonyl)amino)-1,3-Benzenedicarbonyl dichloride

HRID 2249139Notes

Reaction equation

HRID 2249139 reaction equation
[NH2:1][C:2]1[C:3]([I:16])=[C:4]([C:13]([Cl:15])=[O:14])[C:5]([I:12])=[C:6]([C:10]=1[I:11])[C:7]([Cl:9])=[O:8].[CH:17]([CH:20]1[O:25][CH2:24][CH:23]([C:26](Cl)=[O:27])[CH2:22][O:21]1)([CH3:19])[CH3:18]>CC(N(C)C)=O>[CH:17]([CH:20]1[O:25][CH2:24][CH:23]([C:26]([NH:1][C:2]2[C:10]([I:11])=[C:6]([C:7]([Cl:9])=[O:8])[C:5]([I:12])=[C:4]([C:3]=2[I:16])[C:13]([Cl:15])=[O:14])=[O:27])[CH2:22][O:21]1)([CH3:19])[CH3:18]

Participants

4

Reactant 2

HCID 98948585-Amino-2,4,6-triiodoisophthaloyl dichlorideHCID 178822172-(Propan-2-yl)-1,3-dioxane-5-carbonyl chloride

Product 1

HCID 198254472,4,6-triiodo-5-(((2-(1-methylethyl)-1,3-dioxan-5-yl)carbonyl)amino)-1,3-Benzenedicarbonyl dichloride

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

137 g of 5-amino-2,4,6-triiodoisophthaloyl chloride (0.23 mole) are dissolved in 460 ml of DMAC to which are added 110 g (0.57 mole) of 2-isopropyl-1,3-dioxane-5-carboxylic acid chloride. The reaction mixture is stirred under argon at ambient temperature for 4 days. The DMAC is removed in a vacuum. The oil obtained is extracted with 3 l of ethyl acetate and washed twice with 1 l of ice-cold water. The organic phase is dried and concentrated to dryness. The product is crystallized from 200 ml of CH2Cl2. After filtration, 110 g of solid are obtained:

Workup

  1. customThe DMAC is removed in a vacuum
  2. customThe oil obtained
  3. extractionis extracted with 3 l of ethyl acetate
  4. washwashed twice with 1 l of ice-cold water
  5. customThe organic phase is dried
  6. concentrationconcentrated to dryness
  7. customThe product is crystallized from 200 ml of CH2Cl2
  8. filtrationAfter filtration, 110 g of solid
  9. customare obtained

Sources & evidence

ORD record
ord-9e7f88325485421d8187fbf994248911
Source dataset
uspto-grants-1991_08
Patent number
US05043152

Reaction notes

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