Citric Acid → 5-Methoxyacetylamino-2,4,6-triiodisophthalic acid-N,N-bis-(methoxycarbonylmethyl)-amide-chloride

HRID 233422ノート

反応式

HRID 233422 の反応式
COCC([C:6]1[C:7]([I:21])=[C:8](C(Cl)=O)[C:9]([I:17])=[C:10]([C:15]=1[I:16])[C:11]([ClH:13]N)=[O:12])=O.Cl.[CH3:23][O:24][C:25](=[O:33])[CH2:26][NH:27][CH2:28][C:29]([O:31][CH3:32])=[O:30].[CH2:34]([N:36](CC)CC)[CH3:35].C(O)(=O)C[C:43](CC(O)=O)(C(O)=O)[OH:44].[C:54](=[O:57])(O)[O-:55].[Na+].CN(C)C=[O:62]>ClCCl.O>[Cl-:13].[CH3:32][O:31][C:29]([CH2:28][N:27]([CH2:26][C:25]([O:24][CH3:23])=[O:33])[C:11](=[O:12])[C:10]1[C:15]([I:16])=[C:6]([NH:36][C:34](=[O:62])[CH2:35][O:44][CH3:43])[C:7]([I:21])=[C:8]([C:54]([OH:55])=[O:57])[C:9]=1[I:17])=[O:30]

参加物

8

反応物 5

HCID 311Citric AcidHCID 6228DimethylformamideHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 2727727Dimethyl Iminodiacetate Hydrochloride

生成物 1

HCID 867501575-Methoxyacetylamino-2,4,6-triiodisophthalic acid-N,N-bis-(methoxycarbonylmethyl)-amide-chloride

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒

実験手順

A solution of 66.8 g (100 mmol) of 5-methoxyacetyl-amino-2,4,6-triiodoisophthalic acid dichloride (EP 0 015 867) in 300 ml of anhydrous N,N-dimethylformamide is mixed with 21.75 g (110 mmol) of iminodiacetic acid dimethyl ester hydrochloride (synthesis according to Dubsky, Graenacher, Chem. Ber. 50, 1693 (1917)) and 30.5 ml (220 mmol) of triethylamine. A suspension results, which is stirred for 14 hours at room temperature under argon. The batch is taken up in dichloromethane, shaken out once with water, twice with 2N aqueous citric acid and once with aqueous sodium bicarbonate solution. The organic phase is dried on anhydrous magnesium sulfate and concentrated by evaporation in a vacuum. By instilling tert-butyl ether in the concentrated solution, the title compound can precipitate as crystalline solid, which is suctioned off and dried in a vacuum.

後処理

  1. customA suspension results
  2. dry with materialThe organic phase is dried on anhydrous magnesium sulfate
  3. concentrationconcentrated by evaporation in a vacuum
  4. customthe title compound can precipitate as crystalline solid, which
  5. customdried in a vacuum

出典と根拠

ORDレコード
ord-09390b4a2fba4c1da8a2cce57493961f
出典データセット
uspto-grants-1997_01
特許番号
US05593660

反応ノート

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