Acetyl chloride → 5-Acetamido-2,4,6-triiodoisophthaloyl dichloride

HRID 1461609Notes

Reaction equation

HRID 1461609 reaction equation
[NH2:1][C:2]1[C:3]([I:16])=[C:4]([C:13]([Cl:15])=[O:14])[C:5]([I:12])=[C:6]([C:10]=1[I:11])[C:7]([Cl:9])=[O:8].[C:17](Cl)(=[O:19])[CH3:18]>CN(C)C(=O)C>[C:17]([NH:1][C:2]1[C:10]([I:11])=[C:6]([C:7]([Cl:9])=[O:8])[C:5]([I:12])=[C:4]([C:3]=1[I:16])[C:13]([Cl:15])=[O:14])(=[O:19])[CH3:18]

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 98948585-Amino-2,4,6-triiodoisophthaloyl dichloride

Product 1

HCID 111359725-Acetamido-2,4,6-triiodoisophthaloyl dichlorideYield 90%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

5-Amino-2,4,6-triiodoisophthaloyl chloride (190 g,0.32 g-mole) prepared as in Example 1 is dissolved in 475 ml of N,N-dimethylacetamide (DMAc) (dried over molecular sieves), and the solution is stirred and cooled to 0°-3° C. Acetyl chloride (75.1 g, 68 ml, 0.96 g-mole) is added dropwise over a period of 100 minutes, keeping the temperature between 0° C. and 3° C. The ice bath is removed and the solution is stirred overnight at room temperature (20°-25° C.). An additional charge of acetyl chloride (8.5 g, 0.11 g-mole) is added, and the mixture is stirred overnight (23 hours). The product (a creamy white sold) precipitates during this time. The mixture is cooled to 0°-5° C. and filtered while cold. After rinsing with three 100-ml portions of hexane on the funnel, the solution is stirred with three 200-ml portions of cold hexane for 10 minutes each time, collected by suction filtration, and dried in a vacuum desiccator (183 g, 90% yield). The product shows one major spot by TLC analysis.

Workup

  1. temperaturecooled to 0°-3° C
  2. customthe temperature between 0° C. and 3° C
  3. customThe ice bath is removed
  4. stirringthe solution is stirred overnight at room temperature (20°-25° C.)
  5. additionAn additional charge of acetyl chloride (8.5 g, 0.11 g-mole)
  6. additionis added
  7. stirringthe mixture is stirred overnight (23 hours)
  8. customprecipitates during this time
  9. temperatureThe mixture is cooled to 0°-5° C.
  10. filtrationfiltered while cold
  11. washAfter rinsing with three 100-ml portions of hexane on the funnel
  12. stirringthe solution is stirred with three 200-ml portions of cold hexane for 10 minutes each time
  13. filtrationcollected by suction filtration
  14. customdried in a vacuum desiccator (183 g, 90% yield)

Sources & evidence

ORD record
ord-78c40c6eb0a94790a8fdf34c7162b9ab
Source dataset
uspto-grants-1991_12
Patent number
US05075502

Reaction notes

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