Acetic Anhydride → 5-Amino-3-acetoxymethyl-2,4,6-triiodobenzoic acid

HRID 1280147Notes

Reaction equation

HRID 1280147 reaction equation
[NH2:1][C:2]1[C:3]([I:15])=[C:4]([CH2:13][OH:14])[C:5]([I:12])=[C:6]([C:10]=1[I:11])[C:7]([OH:9])=[O:8].[C:16](OC(=O)C)(=[O:18])[CH3:17]>N1C=CC=CC=1>[NH2:1][C:2]1[C:3]([I:15])=[C:4]([CH2:13][O:14][C:16](=[O:18])[CH3:17])[C:5]([I:12])=[C:6]([C:10]=1[I:11])[C:7]([OH:9])=[O:8]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 184291945-Amino-3-hydroxymethyl-2,4,6-triiodobenzoic acid

Product 1

HCID 184293275-Amino-3-acetoxymethyl-2,4,6-triiodobenzoic acidYield 100%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

5-Amino-3-hydroxymethyl-2,4,6-triiodobenzoic acid (41.2 g, 0.076 mol) was dissolved in pyridine (100 ml), and acetic anhydride (80 ml) was added slowly with efficient stirring at room temperature. Stirring was continued overnight. The reaction mixture was then evaporated to a semisolid mass and treated with hydrochloric acid (2M, 250 ml). The white to grey precipitate formed was filtered off and washed with water (2×40 ml) and then dried. 44.2 g (100%) of product was isolated.

Workup

  1. stirringStirring
  2. customThe reaction mixture was then evaporated to a semisolid mass
  3. additiontreated with hydrochloric acid (2M, 250 ml)
  4. customThe white to grey precipitate formed
  5. filtrationwas filtered off
  6. washwashed with water (2×40 ml)
  7. customdried

Sources & evidence

ORD record
ord-96ac6dbe7b5c41f7a8db0ddaa9d79f3b
Source dataset
uspto-grants-2002_09
Patent number
US06448442B1

Reaction notes

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