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

HRID 1613027Notes

Reaction equation

HRID 1613027 reaction equation
IC1C(C(N)=O)=C(I)C=C(I)[C:3]=1[C:4](N)=[O:5].C([O:19][CH2:20][C:21]([NH:23][C:24]1[C:25]([I:54])=[C:26]([C:43]([NH:45][CH2:46][CH:47]([CH2:49][CH:50]([OH:53])[CH2:51][OH:52])[OH:48])=[O:44])[C:27]([I:42])=[C:28]([C:40]=1[I:41])[C:29]([NH:31][CH2:32][CH:33]([CH2:35][CH:36]([OH:39])[CH2:37][OH:38])[OH:34])=[O:30])=[O:22])(=O)C.C([O-])([O-])=O.[K+].[K+].C(OCCBr)(=O)C>CC(N(C)C)=O>[OH:39][CH:36]([CH2:37][OH:38])[CH2:35][CH:33]([OH:34])[CH2:32][NH:31][C:29](=[O:30])[C:28]1[C:40]([I:41])=[C:24]([N:23]([CH2:3][CH2:4][OH:5])[C:21](=[O:22])[CH2:20][OH:19])[C:25]([I:54])=[C:26]([C:43]([NH:45][CH2:46][CH:47]([CH2:49][CH:50]([OH:53])[CH2:51][OH:52])[OH:48])=[O:44])[C:27]=1[I:42]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 135641-Acetoxy-2-bromoethaneHCID 221238242,4,6-TriiodoisophthalamideHCID 867453315-Acetoxyacetamido-N,N'-bis[(2,3-dihydroxypropyl)-2-hydroxyethyl]-2,4,6-triiodoisophthalamide

Product 1

HCID 86745332N,N'-Bis[(2,3-dihydroxypropyl)-2-hydroxyethyl]-5-[N-(2-hydroxyethyl)hydroxyacetamido]-2,4,6-triiodoisophthalamide

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

5[N-(2-Acetoxyethyl)acetoxyacetamido]-N,N'-bis(2,3-dihydroxypropyl)-2-hydroxyethyl]-2,4,6-triiodoisophthalamide. 5-Acetoxyacetamido-N,N'-bis[(2,3-dihydroxypropyl)-2-hydroxyethyl]-2,4,6-triiodoisophthalamide, prepared as in Example 3, Step B, (89 g, 0.1 g-mole) is mixed with K2CO3 (27.6 g, 0.2-g mole) and 2-bromoethyl acetate (33.4 g, 0.2 g-mole) in DMAc (200 ml). The mixture is stirred at 35°-40° C. until the reaction is complete (approximately 8-12 hours). The solution is then cooled to room temperature and the inorganic salts are filtered. The filtrate is then evaporated under vacuum at 70° C. to yield a thick oil. The oil is triturated with isopropyl alcohol to dissolve the residual DMAC and bromoethyl acetate. The supernatant is decanted and the residual solid is evaporated to dryness to provide the desired product.

Workup

  1. custom(approximately 8-12 hours)
  2. filtrationthe inorganic salts are filtered
  3. customThe filtrate is then evaporated under vacuum at 70° C.
  4. customto yield a thick oil
  5. customThe oil is triturated with isopropyl alcohol
  6. dissolutionto dissolve the residual DMAC and bromoethyl acetate
  7. customThe supernatant is decanted
  8. customthe residual solid is evaporated to dryness

Sources & evidence

ORD record
ord-154df0e7a90240068f454989b404beaa
Source dataset
uspto-grants-1993_03
Patent number
US05191120

Reaction notes

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