Methanol → 5-Amino-3-acetoxymethyl-N-(2,3-dihydroxypropyl)-2,4,6-triiodobenzamide

HRID 383030

Reaktionsgleichung

Reaktionsgleichung von HRID 383030
[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)=[O:8].C(=O)([O-])[O-].[Na+].[Na+].[OH:25][CH:26]([CH2:29][OH:30])[CH2:27][NH2:28].CO>O1CCOCC1.O>[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]([NH:28][CH2:27][CH:26]([OH:25])[CH2:29][OH:30])=[O:8]

Komponenten

7

Edukt 4

HCID 887MethanolHCID 10340Sodium CarbonateHCID 735613-Amino-1,2-propanediolHCID 184293385-Amino-3-acetoxymethyl-2,4,6-triiodobenzoyl chloride

Produkt 1

HCID 184291865-Amino-3-acetoxymethyl-N-(2,3-dihydroxypropyl)-2,4,6-triiodobenzamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 312751,4-DioxaneLösungsmittel2×

Versuchsvorschrift

5-Amino-3-acetoxymethyl-2,4,6-triiodobenzoyl chloride (12.0 g, 0.020 mol) was dissolved in 10 ml of dioxane and sodium carbonate (2.1 g, 0.020 mol) was added. To this solution was added a solution of 2,3-dihydroxypropylamine (1.8 g, 0.020 mol) dissolved in 15 ml of dioxane. The mixture was heated to reflux for 10 h. After cooling to room temperature, methanol (25 ml), strongly acidic ion exchange resin (Amberlyst 15, 50 g) and water (25 ml) were added to bring the pH to 3 to 4. After stirring at room temperature for 20 min, the resin was filtered off and the filtrate was evaporated to dryness. The semisolid dark crude product (12.6 g) was acetylated directly in the next step.

Aufarbeitung

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 10 h
  3. filtrationthe resin was filtered off
  4. customthe filtrate was evaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-7214f26c628a44d7909c83153e3de5ad
Quelldatensatz
uspto-grants-2001_10
Patentnummer
US06310243B1

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