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

HRID 1291971ノート

反応式

HRID 1291971 の反応式
[CH3:1][O:2][CH2:3][C:4]([NH:6][C:7]1[C:8]([I:21])=[C:9]([C:18](Cl)=[O:19])[C:10]([I:17])=[C:11]([C:15]=1[I:16])[C:12]([Cl:14])=[O:13])=[O:5].Cl.[CH3:23][O:24][C:25](=[O:33])[CH2:26][NH:27][CH2:28][C:29]([O:31][CH3:32])=[O:30].C(N(CC)CC)C.C(O)(=O)CC(CC(O)=O)(C(O)=O)[OH:44].C(=O)(O)[O-].[Na+]>CN(C)C=O.ClCCl.O>[Cl-:14].[CH3:32][O:31][C:29]([CH2:28][N:27]([CH2:26][C:25]([O:24][CH3:23])=[O:33])[C:18](=[O:19])[C:9]1[C:8]([I:21])=[C:7]([NH:6][C:4](=[O:5])[CH2:3][O:2][CH3:1])[C:15]([I:16])=[C:11]([C:12]([OH:44])=[O:13])[C:10]=1[I:17])=[O:30]

参加物

9

反応物 5

HCID 311Citric AcidHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 2727727Dimethyl Iminodiacetate HydrochlorideHCID 135899615-Methoxyacetamido-2,4,6-triiodoisophthaloyl chloride

生成物 1

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

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒

実験手順

A solution of 66.8 g (100 mmol) of 5-methoxyacetylamino-2,4,6-triiodisophthalic acid dichloride (EP 0015867) 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 instillation of tert-butyl ether in the concentrated solution, the title compound can be precipitated 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. customBy instillation of tert-butyl ether in the concentrated solution, the title compound can be precipitated as crystalline solid, which
  5. customdried in a vacuum

出典と根拠

ORDレコード
ord-00d55bd08aaa4746bdd3ccdcc710804b
出典データセット
uspto-grants-1998_05
特許番号
US05756066

反応ノート

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