Thionyl Chloride → HCID 87853775, compound

HRID 1271815Notes

Reaction equation

HRID 1271815 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].[CH3:33]C(N(C)C)=O>>[I:28][C:21]1[C:20]([C:29]([Cl:31])=[O:30])=[C:19]([I:32])[C:18]([N:17]([CH3:33])[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 4

HCID 24386Thionyl ChlorideHCID 31374DimethylacetamideHCID 98948585-Amino-2,4,6-triiodoisophthaloyl dichlorideHCID 18454895HCID 18454895, compound

Product 1

HCID 87853775HCID 87853775, compound

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, 24.4 g (40 mmol) of 5-amino-2,4,6-triiodoisophthalic acid dichloride (EP 0033426, Sovak, 1/80 US) is added at 0° C., and it is stirred for 4 days at room temperature. The reaction mixture is poured into 5 liters 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. filtrationthe solid that accumulates is filtered off
  2. customFor further purification
  3. dissolutionthe filter residue is dissolved in 1000 ml of ethyl acetate
  4. stirringshaken out twice with saturated sodium bicarbonate solution
  5. customthe organic phase is dried on sodium sulfate
  6. concentrationthe solvent is concentrated by evaporation in a vacuum

Sources & evidence

ORD record
ord-46c7f54098c9420e929a33f6b67973e7
Source dataset
uspto-grants-2007_04
Patent number
US07208140B2

Reaction notes

Loading…