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

HRID 1280173노트

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HRID 1280173 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 312751,4-Dioxane용매

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온도
90 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-2d71ad42d9b54dce98042a53053e360b
출처 데이터셋
uspto-grants-2002_09
특허 번호
US06448442B1

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