2-Chloroethanol → HCID 86745333, compound

HRID 1461613Notes

Reaction equation

HRID 1461613 reaction equation
[C:1]([NH:4][C:5]1[C:6]([I:35])=[C:7]([C:24]([NH:26][CH2:27][CH:28]([CH2:30][CH:31]([OH:34])[CH2:32][OH:33])[OH:29])=[O:25])[C:8]([I:23])=[C:9]([C:21]=1[I:22])[C:10]([NH:12][CH2:13][CH:14]([CH2:16][CH:17]([OH:20])[CH2:18][OH:19])[OH:15])=[O:11])(=[O:3])[CH3:2].Cl[CH2:37][CH2:38][OH:39].OS(O)(=O)=O>[OH-].[Na+]>[OH:34][CH:31]([CH2:32][OH:33])[CH2:30][CH:28]([OH:29])[CH2:27][NH:26][C:24](=[O:25])[C:7]1[C:6]([I:35])=[C:5]([N:4]([CH2:37][CH2:38][OH:39])[C:1](=[O:3])[CH3:2])[C:21]([I:22])=[C:9]([C:10]([NH:12][CH2:13][CH:14]([CH2:16][CH:17]([OH:20])[CH2:18][OH:19])[OH:15])=[O:11])[C:8]=1[I:23]

Participants

5

Reactant 3

HCID 342-ChloroethanolHCID 1118Sulfuric AcidHCID 86745334HCID 86745334, compound

Product 1

HCID 86745333HCID 86745333, compound

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

5-Acetamido-N,N'-bis[(2,3-dihydroxypropyl)-2-hydroxyethyl]-2,4,6-triiodoisophthalamide, prepared as in Example 2, Step B, (83.5 g, 0.1 g-mole) is dissolved in 1 N NaOH (140 ml, 0.14 g-mole) and the solution is stirred at room temperature for 1 hour and 2-chloroethanol (13.7 g, 0.17 g-mole) is added. The solution is stirred at 50° C. for 5 hours to complete the reaction. The solution is acidified with H2SO4 and evaporated to dryness under reduced pressure. The residue is triturated with MeOH and the precipitated solid is filtered. The mother liquor is concentrated under vacuum and the crude product is purified by reverse-phase (C18) HPLC to give the purified final product. The yield of this reaction and purification is 80%.

Workup

  1. stirringThe solution is stirred at 50° C. for 5 hours
  2. customthe reaction
  3. customevaporated to dryness under reduced pressure
  4. customThe residue is triturated with MeOH
  5. filtrationthe precipitated solid is filtered
  6. concentrationThe mother liquor is concentrated under vacuum
  7. customthe crude product is purified by reverse-phase (C18) HPLC
  8. customto give the
  9. custompurified final product
  10. customThe yield of this reaction and purification

Sources & evidence

ORD record
ord-e6a7aea994124c7488d549ae0ae70db4
Source dataset
uspto-grants-1991_12
Patent number
US05075502

Reaction notes

Loading…