Dimethylacetamide → HCID 54457487, compound

HRID 2163148Notes

Reaction equation

HRID 2163148 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][C:7](Cl)=[O:8].[NH2:10][C:11]1[C:12]([I:29])=[C:13]([C:22]([NH:24][CH2:25][CH:26]([OH:28])[CH3:27])=[O:23])[C:14]([I:21])=[C:15]([C:19]=1[I:20])[C:16]([OH:18])=[O:17].CC(N(C)C)=O>O>[OH:28][CH:26]([CH3:27])[CH2:25][NH:24][C:22](=[O:23])[C:13]1[C:14]([I:21])=[C:15]([C:19]([I:20])=[C:11]([NH:10][C:7](=[O:8])[CH2:6][O:5][CH2:4][CH2:3][O:2][CH3:1])[C:12]=1[I:29])[C:16]([OH:18])=[O:17]

Participants

5

Reactant 3

HCID 31374DimethylacetamideHCID 70103382-(2-Methoxyethoxy)acetyl chlorideHCID 22754106HCID 22754106, compound

Product 1

HCID 54457487HCID 54457487, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

At a maximum of 10° C. (ice cooling), 16.5 ml. of methoxyethoxyacetyl chloride is added dropwise within 30 minutes with agitation to 30.8 g. (50 mmol) of 5-amino-(2-hydroxypropyl)2,4,6-triiodoisophthalamic acid in 60 ml. of dimethylacetamide. The mixture is stirred for 1 hour at 0° C. and then for 16 hours at room temperature. Thereafter, another 2 ml. of the acid chloride is added thereto, and the mixture is stirred at room temperature for 4 hours. Then, 10 ml. of water is added and the mixture is concentrated under vacuum. The residue is dissolved in 350 ml. of water and neutralized with 32% sodium hydroxide solution. The mixture is combined with another 5 ml. of 32% sodium hydroxide solution and then stirred for some time after adding 5 g. of active carbon. After the carbon has been removed, the mixture is acidified with concentrated hydrochloric acid, allowed to stand for a period of time and vacuum-filtered. The resulting precipitate is dried under vacuum. Yield: 21.3 g. (58%), m.p. 275° C., with decomposition.

Workup

  1. customAt a maximum of 10° C. (ice cooling), 16.5 ml
  2. waitfor 16 hours at room temperature
  3. stirringthe mixture is stirred at room temperature for 4 hours
  4. concentrationthe mixture is concentrated under vacuum
  5. dissolutionThe residue is dissolved in 350 ml
  6. stirringof 32% sodium hydroxide solution and then stirred for some time
  7. additionafter adding 5 g
  8. customAfter the carbon has been removed
  9. waitto stand for a period of time
  10. filtrationvacuum-filtered
  11. customThe resulting precipitate is dried under vacuum

Sources & evidence

ORD record
ord-7c2cf837d3c14dad9929e58c28c6bc45
Source dataset
uspto-grants-1979_01
Patent number
US04132731

Reaction notes

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