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

HRID 1280149

반응식

HRID 1280149 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(=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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 312751,4-Dioxane용매2회

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-64efdb4816ba41d3be32188ede282bdd
출처 데이터셋
uspto-grants-2002_09
특허 번호
US06448442B1

연결된 노트

불러오는 중…