2,3,5-Triiodobenzoic acid → 2-(2',3',5'-Triiodobenzoyl)ethyl methacrylate

HRID 1489782Notes

Reaction equation

HRID 1489782 reaction equation
[I:1][C:2]1[C:10]([I:11])=[CH:9][C:8]([I:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[C:13]([O:18][CH2:19][CH2:20]O)(=[O:17])[C:14]([CH3:16])=[CH2:15].C1(N=C=NC2CCCCC2)CCCCC1>CCOCC>[C:13]([O:18][CH2:19][CH2:20][O:5][C:4](=[O:6])[C:3]1[CH:7]=[C:8]([I:12])[CH:9]=[C:10]([I:11])[C:2]=1[I:1])(=[O:17])[C:14]([CH3:16])=[CH2:15]

Participants

5

Reactant 3

HCID 69482,3,5-Triiodobenzoic acidHCID 10868DicyclohexylcarbodiimideHCID 133602-Hydroxyethyl Methacrylate

Product 1

HCID 1279202-(2',3',5'-Triiodobenzoyl)ethyl methacrylate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

2,3,5-triiodobenzoic acid (25 g), 2-hydroxyethyl methacrylate (7.2 g), 1,3-dicyclohexylcarbodiimide (11.5 g) and 4-pyrrilidinopyridine (0.75 g) were stirred in ether suspension (250 ml) at room temperature for 24 hr. The solid was filtered off and the residue washed with fresh ether. The ether solution was extracted with dilute HCl (0.2M) and then with saturated sodium bicarbonate solution. The organic phase was dried (MgSO4) and the solvent removed under reduced pressure. The residue (21.1 g) was recrystallised from ethyl acetate to give a pure material as white crystals m.pt.94° C.

Workup

  1. filtrationThe solid was filtered off
  2. washthe residue washed with fresh ether
  3. extractionThe ether solution was extracted with dilute HCl (0.2M)
  4. dry with materialThe organic phase was dried (MgSO4)
  5. customthe solvent removed under reduced pressure
  6. customThe residue (21.1 g) was recrystallised from ethyl acetate

Sources & evidence

ORD record
ord-2e37457405754a8abf038e4a76377170
Source dataset
uspto-grants-1997_10
Patent number
US05679710

Reaction notes

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