Sulfuric Acid → 5-Acetamido-2,4,6-triiodoisophthaloyl dichloride

HRID 1660112Notes

Reaction equation

HRID 1660112 reaction equation
[C:1](OC(=O)C)(=[O:3])[CH3:2].S(=O)(=O)(O)O.[NH2:13][C:14]1[C:15]([I:28])=[C:16]([C:25]([Cl:27])=[O:26])[C:17]([I:24])=[C:18]([C:22]=1[I:23])[C:19]([Cl:21])=[O:20]>C1C=CC=CC=1.CC(C)=O>[C:1]([NH:13][C:14]1[C:22]([I:23])=[C:18]([C:19]([Cl:21])=[O:20])[C:17]([I:24])=[C:16]([C:15]=1[I:28])[C:25]([Cl:27])=[O:26])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 7918Acetic AnhydrideHCID 98948585-Amino-2,4,6-triiodoisophthaloyl dichloride

Product 1

HCID 111359725-Acetamido-2,4,6-triiodoisophthaloyl dichloride

Reagents, catalysts & solvents 1

HCID 22015841Benzene methyl ketoneSolvent

Procedure

A mixture of 50 ml. of acetic anhydride and 0.1 ml. of conc. sulfuric acid was stirred at room temperature for 5 minutes. To this mixture was added 15 g. (0.025 mole) of 5-amino-2,4,6-triiodoisophthaloyl chloride in one portion and stirring was continued at room temperature for one hour. The mixture was stored overnight at 0°. Filtration furnished 16 g. of solid material. The product was recrystallized from ethyl acetate to furnish 10 g. (63%) of pure product. The compound was shown to be pure by tlc (silica plate-benzene/acetone 80/20).

Workup

  1. additionA mixture of 50 ml
  2. additionTo this mixture was added 15 g
  3. waitThe mixture was stored overnight at 0°
  4. filtrationFiltration
  5. customfurnished 16 g
  6. customThe product was recrystallized from ethyl acetate
  7. customto furnish 10 g

Sources & evidence

ORD record
ord-5a28e8073d69468e92ff6f7f68aeb4b5
Source dataset
uspto-grants-1981_12
Patent number
US04307072

Reaction notes

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