Sodium Carbonate → N,N'-Bis[(2,3-dihydroxypropyl)-2-hydroxyethyl]-5-hydroxyacetamido-2,4,6-triiodoisophthalamide

HRID 1613026

反応式

HRID 1613026 の反応式
C([O:4][CH2:5][C:6]([NH:8][C:9]1[C:10]([I:39])=[C:11]([C:28]([NH:30][CH2:31][CH:32]([CH2:34][CH:35]([OH:38])[CH2:36][OH:37])[OH:33])=[O:29])[C:12]([I:27])=[C:13]([C:25]=1[I:26])[C:14]([NH:16][CH2:17][CH:18]([CH2:20][CH:21]([OH:24])[CH2:22][OH:23])[OH:19])=[O:15])=[O:7])(=O)C.C(OCC(NC1C(I)=C(C(Cl)=O)C(I)=C(C=1I)C(Cl)=O)=O)(=O)C.C([O-])([O-])=O.[Na+].[Na+].OCCNCC(O)CO>CC(N(C)C)=O.CCOC(C)=O.C(Cl)Cl>[OH:24][CH:21]([CH2:22][OH:23])[CH2:20][CH:18]([OH:19])[CH2:17][NH:16][C:14](=[O:15])[C:13]1[C:25]([I:26])=[C:9]([NH:8][C:6](=[O:7])[CH2:5][OH:4])[C:10]([I:39])=[C:11]([C:28]([NH:30][CH2:31][CH:32]([CH2:34][CH:35]([OH:38])[CH2:36][OH:37])[OH:33])=[O:29])[C:12]=1[I:27]

参加物

7

反応物 4

HCID 10340Sodium CarbonateHCID 129431915-[[2-(Acetyloxy)acetyl]amino]-2,4,6-triiodo-1,3-benzenedicarbonyl dichlorideHCID 150349453-[(2-Hydroxyethyl)amino]propane-1,2-diolHCID 867453315-Acetoxyacetamido-N,N'-bis[(2,3-dihydroxypropyl)-2-hydroxyethyl]-2,4,6-triiodoisophthalamide

生成物 1

HCID 86745330N,N'-Bis[(2,3-dihydroxypropyl)-2-hydroxyethyl]-5-hydroxyacetamido-2,4,6-triiodoisophthalamide収率 86%

試薬・触媒・溶媒 2

HCID 31374Dimethylacetamide溶媒2 回HCID 21226138Dichloromethane ethylacetate溶媒

実験手順

5-Acetoxyacetamido-N,N'-bis[(2,3-dihydroxypropyl)-2-hydroxyethyl]-2,4,6-triiodoisophthalamide. 69 g (0.1 g-mole) of 5-acetoxyacetamido-2,4,6-triiodoisophthaloyl chloride is dissolved in DMAc (140 ml) and anhydrous Na2CO3 (31.8 g, 0.3 g-mole) is added. To the solution, a DMAc solution (87 ml) containing 26.2 g (0.3 g-mole) of 3-(N-2-hydroxyethyl)amino-1,2-propanediol is added. The mixture is heated and stirred at 35°-40° C. until the reaction is completed as determined by the TLC analysis (EtOAc/CH2Cl2 ; 30/20). After the reaction, the inorganic salts are filtered and the filtrate containing the desired product is evaporated to dryness to give a gum. The gum is triturated with isopropyl alcohol to dissolve the excess amino-triol. The clear supernatant is decanted and the residual solid is dissolved in water (150 ml), treated with Amberlite® IR-120H resin and evaporated to dryness to give the desired product (77 g, 86% yield).

後処理

  1. additionis added
  2. temperatureThe mixture is heated
  3. customAfter the reaction
  4. filtrationthe inorganic salts are filtered
  5. additionthe filtrate containing the desired product
  6. customis evaporated to dryness
  7. customto give a gum
  8. customThe gum is triturated with isopropyl alcohol
  9. dissolutionto dissolve the excess amino-triol
  10. customThe clear supernatant is decanted
  11. dissolutionthe residual solid is dissolved in water (150 ml)
  12. additiontreated with Amberlite® IR-120H resin
  13. customevaporated to dryness

出典と根拠

ORDレコード
ord-c9182094a13a4c148242f82ef5717257
出典データセット
uspto-grants-1993_03
特許番号
US05191120

関連ノート

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