Thionyl Chloride → 5-Amino-3-acetoxymethyl-2,4,6-triiodobenzoyl chloride

HRID 383029Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 383029
[NH2:1][C:2]1[C:3]([I:18])=[C:4]([CH2:13][O:14][C:15](=[O:17])[CH3:16])[C:5]([I:12])=[C:6]([C:10]=1[I:11])[C:7](O)=[O:8].S(Cl)([Cl:21])=O>ClCCCl>[NH2:1][C:2]1[C:3]([I:18])=[C:4]([CH2:13][O:14][C:15](=[O:17])[CH3:16])[C:5]([I:12])=[C:6]([C:10]=1[I:11])[C:7]([Cl:21])=[O:8]

Komponenten

4

Edukt 2

HCID 24386Thionyl ChlorideHCID 184293275-Amino-3-acetoxymethyl-2,4,6-triiodobenzoic acid

Produkt 1

HCID 184293385-Amino-3-acetoxymethyl-2,4,6-triiodobenzoyl chloride

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 111,2-DichloroethaneLösungsmittel

Versuchsvorschrift

5-Amino-3-acetoxymethyl-2,4,6-triiodobenzoic acid (43.9 g, 0.075 mol) was suspended in 1,2-dichloroethane (40 ml) and thionyl chloride (24.9 ml, 0.34 mol) was added. The mixture was heated to reflux temperature for 3 h. After evaporation to dryness, the residue was dissolved in tetrahydrofuran (50 ml). Sodium hydrogen carbonate (15 g) and crystalline sodium carbonate (5 g) were added to the solution and the mixture was stirred at room temperature for 3 h. The mixture was filtered and the filtrate evaporated to dryness. After pump-drying, a foam was formed, yield 44.6 g (98%). This material was used directly in the next step.

Aufarbeitung

  1. temperatureThe mixture was heated
  2. temperatureto reflux temperature for 3 h
  3. customAfter evaporation to dryness
  4. dissolutionthe residue was dissolved in tetrahydrofuran (50 ml)
  5. additionSodium hydrogen carbonate (15 g) and crystalline sodium carbonate (5 g) were added to the solution
  6. filtrationThe mixture was filtered
  7. customthe filtrate evaporated to dryness
  8. customAfter pump-drying
  9. customa foam was formed

Quellen und Nachweise

ORD-Eintrag
ord-ef298e2cbb1348f4b64e4b77f060c514
Quelldatensatz
uspto-grants-2001_10
Patentnummer
US06310243B1

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