Toluene → 5-Amino-2,4,6-triiodoisophthaloyl dichloride

HRID 1290322Notes

Reaction equation

HRID 1290322 reaction equation
[Cl-:1].[Cl:2]C1N(C)CC[NH+]1C.[NH2:10][C:11]1[C:12]([I:25])=[C:13]([C:22](O)=[O:23])[C:14]([I:21])=[C:15]([C:19]=1[I:20])[C:16](O)=[O:17].C1(C)C=CC=CC=1>CCCCCC>[NH2:10][C:11]1[C:12]([I:25])=[C:13]([C:22]([Cl:2])=[O:23])[C:14]([I:21])=[C:15]([C:19]=1[I:20])[C:16]([Cl:1])=[O:17]

Participants

5

Reactant 3

HCID 1140TolueneHCID 30157835-Amino-2,4,6-triiodo-1,3-benzenedicarboxylic acidHCID 109867151H-Imidazolium, 2-chloro-4,5-dihydro-1,3-dimethyl-, chloride

Product 1

HCID 98948585-Amino-2,4,6-triiodoisophthaloyl dichlorideYield 95%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

To a reaction flask, 4.23 g (0.025 mole) of 2-chloro-1,3-dimethylimidazolinium chloride, 5.58 g (0.01 mole) of 5-amino-2,4,6-triiodoisophthalic acid and 80 g of toluene were charged and reacted at 105°-110° C. for 4 hours. Thereafter, the reaction mass was cooled and toluene was removed under reduced pressure. To the concentrate thus obtained, 100 ml of hexane was added to crystallize 5-amino-2,4,6-triiodoisophthaloyl dichloride. The precipitate was filtered and dried under reduced pressure to obtain 5.65 g (95% yield) of 5-amino-2,4,6-triiodoisophthaloyl dichloride as white crystals.

Workup

  1. customreacted at 105°-110° C. for 4 hours
  2. temperatureThereafter, the reaction mass was cooled
  3. customtoluene was removed under reduced pressure
  4. concentrationTo the concentrate thus
  5. customobtained
  6. customto crystallize 5-amino-2,4,6-triiodoisophthaloyl dichloride
  7. filtrationThe precipitate was filtered
  8. customdried under reduced pressure

Sources & evidence

ORD record
ord-5d5d0b90f425497b8b534eb2e05a9523
Source dataset
uspto-grants-1998_05
Patent number
US05750779

Reaction notes

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