Acetoxyacetyl chloride → HCID 22754108, compound

HRID 2163149Notes

Reaction equation

HRID 2163149 reaction equation
C([O:4][CH2:5][C:6](Cl)=[O:7])(=O)C.[NH2:9][C:10]1[C:11]([I:28])=[C:12]([C:21]([NH:23][CH2:24][CH:25]([OH:27])[CH3:26])=[O:22])[C:13]([I:20])=[C:14]([C:18]=1[I:19])[C:15]([OH:17])=[O:16].CC(N(C)C)=O>O>[OH:4][CH2:5][C:6]([NH:9][C:10]1[C:11]([I:28])=[C:12]([C:21]([NH:23][CH2:24][CH:25]([OH:27])[CH3:26])=[O:22])[C:13]([I:20])=[C:14]([C:18]=1[I:19])[C:15]([OH:17])=[O:16])=[O:7]

Participants

5

Reactant 3

HCID 26297Acetoxyacetyl chlorideHCID 31374DimethylacetamideHCID 22754106HCID 22754106, compound

Product 1

HCID 22754108HCID 22754108, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

At temperatures no higher than 10° C., 13.3 ml. of acetoxyacetyl chloride is gradually added dropwise with agitation to a solution of 30.8 g. (50 mmol) of 5-amino-(2-hydroxypropyl)-2,4,6-triiodoisophthalamic acid in 60 ml. of dimethylacetamide. After 16 hours of agitation at room temperature and the addition of 10 ml. of water, the mixture is stirred for 30 minutes at room temperature and then concentrated under vacuum. The residue, after having been treated repeatedly with fresh water, is saponified on a steam bath with agitation with 70 ml. of 2N sodium hydroxide solution in 250 ml. of water. After cooling, the reaction mixture is acidified with 12.5 ml. of concentrated hydrochloric acid, stirred for 16 hours at room temperature, and, after adding approximately the same volume of saturated NaCl solution, allowed to stand for 4 days. Thereafter, the mixture is vacuum-filtered from the thus-separated precipitate, which is washed with minimum portions of water and dried under vacuum. Yield: 17.2 g. (51%), m.p. 275°-277° C., with decomposition.

Workup

  1. customno higher than 10° C., 13.3 ml
  2. additionthe addition of 10 ml
  3. concentrationconcentrated under vacuum
  4. additionThe residue, after having been treated repeatedly with fresh water
  5. customis saponified on a steam bath with agitation with 70 ml
  6. temperatureAfter cooling
  7. additionafter adding approximately the same volume of saturated NaCl solution
  8. waitto stand for 4 days
  9. filtrationThereafter, the mixture is vacuum-filtered from the thus-separated precipitate, which
  10. washis washed with minimum portions of water
  11. customdried under vacuum

Sources & evidence

ORD record
ord-879d6f90f31c48458763f1c4f7e87adf
Source dataset
uspto-grants-1979_01
Patent number
US04132731

Reaction notes

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