Water → HCID 23373570, compound

HRID 865903Notes

Reaction equation

HRID 865903 reaction equation
[NH2:1][C:2]1[C:3]([I:16])=[C:4]([C:13]([OH:15])=[O:14])[C:5]([I:12])=[C:6]([C:9]([OH:11])=[O:10])[C:7]=1[I:8].[OH2:17]>CC(N(C)C)=O>[C:13]([CH2:4][CH2:5][CH2:6][C:9]([NH:1][C:2]1[C:7]([I:8])=[C:6]([C:9]([OH:11])=[O:10])[C:5]([I:12])=[C:4]([C:13]([OH:15])=[O:14])[C:3]=1[I:16])=[O:10])([OH:14])=[O:17]

Participants

4

Reactant 2

HCID 962WaterHCID 30157835-Amino-2,4,6-triiodo-1,3-benzenedicarboxylic acid

Product 1

HCID 23373570HCID 23373570, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

To an ice cool stirred solution of 5-amino-2,4,6-triiodo-1,3-benzenedicarboxylic acid, diacid chloride (2.7 g, 4.6 mmol) in 3 mL of dimethylacetamide was added methyl (4-chloroformyl)butyrate (1.5 g, 9.0 mmol). The solution was stirred for 18 hours at room temperature. The reaction mixture ws poured into 25 mL of water and extracted with 3×15 mL of ethyl acetate. The combined organic phase was extracted with 2×10 mL of water, dried over anhydrous magnesium sulfate, filtered and evaporated in vacuo to afford the desired product as a residue. The crude product was crystallized from CH3CN to yield 1.35 g of the title A compound, i.e., the isophthalyl chloride. The product was used without further purification.

Workup

  1. extractionextracted with 3×15 mL of ethyl acetate
  2. extractionThe combined organic phase was extracted with 2×10 mL of water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-fb9038508470457796c2f825318d81fa
Source dataset
uspto-grants-1996_10
Patent number
US05569446

Reaction notes

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