Thionyl Chloride → HCID 87854393, compound

HRID 1271814Notes

Reaction equation

HRID 1271814 reaction equation
S(Cl)(Cl)=O.[F:5][C:6]([F:11])([F:10])[C:7](O)=[O:8].[NH2:12][CH2:13][C:14]([OH:16])=O.[NH2:17][C:18]1[C:19]([I:32])=[C:20]([C:29]([Cl:31])=[O:30])[C:21]([I:28])=[C:22]([C:26]=1[I:27])[C:23]([Cl:25])=[O:24]>CC(N(C)C)=O>[I:28][C:21]1[C:20]([C:29]([Cl:31])=[O:30])=[C:19]([I:32])[C:18]([NH:17][C:14](=[O:16])[CH2:13][NH:12][C:7](=[O:8])[C:6]([F:11])([F:10])[F:5])=[C:26]([I:27])[C:22]=1[C:23]([Cl:25])=[O:24]

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 98948585-Amino-2,4,6-triiodoisophthaloyl dichlorideHCID 18454895HCID 18454895, compound

Product 1

HCID 87854393HCID 87854393, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

14.5 ml (200 mmol) of thionyl chloride is added in drops at 0° C. within 1 hour to a solution of 34.2 g (200 mmol) of glycine trifluoroacetate in 200 ml of dimethylacetamide. Then, 23.8 g (40 mmol) of 5-amino-2,4,6-triiodoisophthalic acid dichloride (DE 2943777, Schering AG, (priority: Oct. 26, 1979)) is added at 0° C. and stirred for 4 days at room temperature. The reaction mixture is poured into 5liters of ice water and the solid that accumulates is filtered off. For further purification, the filter residue is dissolved in 1000 ml of ethyl acetate, shaken out twice with saturated sodium bicarbonate solution, the organic phase is dried on sodium sulfate, and the solvent is concentrated by evaporation in a vacuum.

Workup

  1. addition26, 1979)) is added at 0° C.
  2. filtrationthe solid that accumulates is filtered off
  3. customFor further purification
  4. dissolutionthe filter residue is dissolved in 1000 ml of ethyl acetate
  5. stirringshaken out twice with saturated sodium bicarbonate solution
  6. customthe organic phase is dried on sodium sulfate
  7. concentrationthe solvent is concentrated by evaporation in a vacuum

Sources & evidence

ORD record
ord-7da53ca7164f444e89e78a86c8e65b4f
Source dataset
uspto-grants-2007_04
Patent number
US07208140B2

Reaction notes

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