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

HRID 383031Notes

Reaction equation

HRID 383031 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-2e2428e82c804b1db3bc88d0bf60ba2a
Source dataset
uspto-grants-2001_10
Patent number
US06310243B1

Reaction notes

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