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

HRID 1280173ノート

反応式

HRID 1280173 の反応式
[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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
90 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-2d71ad42d9b54dce98042a53053e360b
出典データセット
uspto-grants-2002_09
特許番号
US06448442B1

反応ノート

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