Acetonitrile → 5-Amino-3-acetoxymethyl-N,N-bis-(2,3-dihydroxypropyl)-2,4,6-triiodo-benzamide

HRID 1280173

Reaktionsgleichung

Reaktionsgleichung von HRID 1280173
[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(N(CC)CC)C.[OH:26][CH:27]([CH2:35][OH:36])[CH2:28][NH:29][CH2:30][CH:31]([OH:34])[CH2:32][OH:33].C(#N)C>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]([N:29]([CH2:28][CH:27]([OH:26])[CH2:35][OH:36])[CH2:30][CH:31]([OH:34])[CH2:32][OH:33])=[O:8]

Komponenten

7

Edukt 4

HCID 6342AcetonitrileHCID 8471TriethylamineHCID 184035543,3'-Iminobispropane-1,2-diolHCID 184293385-Amino-3-acetoxymethyl-2,4,6-triiodobenzoyl chloride

Produkt 1

HCID 184293315-Amino-3-acetoxymethyl-N,N-bis-(2,3-dihydroxypropyl)-2,4,6-triiodo-benzamideAusbeute 93 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

5-Amino-3-acetoxymethyl-2,4,6-triiodobenzoyl chloride (19.9 g, 32.9 mmol) was dissolved in dioxane (45 ml) and triethylamine (3.32 g, 32.9 mmol) was added. To this solution was added bis-(2,3-dihydroxypropyl)amine (5.43 g, 32.9 mmol), and the mixture was stirred at 90° C. for 17 h. After cooling to room temperature, acetonitrile (150 ml), water (70 ml), and a strongly acidic ion exchange resin (Amberlyst 15, 60 g) were added to bring the pH to 4. After stirring at room temperature for 20 min, the resin was filtered off and the filtrate was evaporated to dryness. The semicrystalline dark residue was filtered through a short column of silica using a mixture of methylene chloride and methanol (70/30) as the eluent. The solvent was evaporated and 22.4 g (93%) of a tan coloured crystalline product was obtained. This product was acetylated without further purification.

Aufarbeitung

  1. temperatureAfter cooling to room temperature
  2. stirringAfter stirring at room temperature for 20 min
  3. filtrationthe resin was filtered off
  4. customthe filtrate was evaporated to dryness
  5. filtrationThe semicrystalline dark residue was filtered through a short column of silica using
  6. additiona mixture of methylene chloride and methanol (70/30) as the eluent
  7. customThe solvent was evaporated

Quellen und Nachweise

ORD-Eintrag
ord-2d71ad42d9b54dce98042a53053e360b
Quelldatensatz
uspto-grants-2002_09
Patentnummer
US06448442B1

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