Acetic Anhydride → 3-Acetoxymethyl-5-(2,3-diacetoxypropylaminocarbonyl)-2,4,6-triiodoaniline

HRID 1604173Notes

Reaction equation

HRID 1604173 reaction equation
[NH2:1][C:2]1[C:3]([I:23])=[C:4]([CH2:18][O:19][C:20](=[O:22])[CH3:21])[C:5]([I:17])=[C:6]([C:15]=1[I:16])[C:7]([NH:9][CH2:10][CH:11]([OH:14])[CH2:12][OH:13])=[O:8].[C:24](OC(=O)C)(=[O:26])[CH3:25].C(Cl)Cl.[C:34](OCC)(=[O:36])[CH3:35]>N1C=CC=CC=1>[NH2:1][C:2]1[C:3]([I:23])=[C:4]([CH2:18][O:19][C:20](=[O:22])[CH3:21])[C:5]([I:17])=[C:6]([C:15]=1[I:16])[C:7]([NH:9][CH2:10][CH:11]([O:14][C:34](=[O:36])[CH3:35])[CH2:12][O:13][C:24](=[O:26])[CH3:25])=[O:8]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 184291865-Amino-3-acetoxymethyl-N-(2,3-dihydroxypropyl)-2,4,6-triiodobenzamideHCID 21226138Dichloromethane ethylacetate

Product 1

HCID 184291303-Acetoxymethyl-5-(2,3-diacetoxypropylaminocarbonyl)-2,4,6-triiodoaniline

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

5-Amino-3-acetoxymethyl-N-(2,3-dihydroxypropyl)-2,4,6-triiodobenzamide (2.13 g, 3.23 mmol) was dissolved in pyridine (12 ml). Acetic anhydride (10 ml) was added dropwise with efficient stirring. Stirring was continued at ambient temperature for 10 h. The reaction mixture was then evaporated to a solid residue, which was taken up in chloroform (70 ml). The organic phase was washed with aqueous hydrochloric acid (1M) until pH=2, then twice with water (40 ml) and last with a saturated solution of sodium hydrogen carbonate until pH=8-9. After drying (Na2SO4), the solvent was evaporated to yield a dark solid residue. This was taken up in a mixture of methylene chloride/ethyl acetate (90/10) and eluted through a pad of alumina. After evaporation of the solvent, 2.1 g (87%) of a white crystalline residue was left.

Workup

  1. customThe reaction mixture was then evaporated to a solid residue, which
  2. washThe organic phase was washed with aqueous hydrochloric acid (1M) until pH=2
  3. dry with materialAfter drying (Na2SO4)
  4. customthe solvent was evaporated
  5. customto yield a dark solid residue
  6. washeluted through a pad of alumina
  7. customAfter evaporation of the solvent, 2.1 g (87%) of a white crystalline residue
  8. waitwas left

Sources & evidence

ORD record
ord-4df6a58c0bef49b0bf483d1e27b76921
Source dataset
uspto-grants-1999_11
Patent number
US05993780

Reaction notes

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