Boric Acid → 5-(N-allylacetamido)-N1,N3-bis(2,3-dihydroxypropyl)-2,4,6-triiodoisophthalamide

HRID 1408286

Reaction equation

HRID 1408286 reaction equation
[C:1]([NH:4][C:5]1[C:6]([I:29])=[C:7]([C:21]([NH:23][CH2:24][CH:25]([OH:28])[CH2:26][OH:27])=[O:22])[C:8]([I:20])=[C:9]([C:18]=1[I:19])[C:10]([NH:12][CH2:13][CH:14]([OH:17])[CH2:15][OH:16])=[O:11])(=[O:3])[CH3:2].B(O)(O)O.[OH-].[K+].[CH2:36](Br)[CH:37]=[CH2:38]>O.CO>[CH2:38]([N:4]([C:5]1[C:18]([I:19])=[C:9]([C:10]([NH:12][CH2:13][CH:14]([OH:17])[CH2:15][OH:16])=[O:11])[C:8]([I:20])=[C:7]([C:6]=1[I:29])[C:21]([NH:23][CH2:24][CH:25]([OH:28])[CH2:26][OH:27])=[O:22])[C:1](=[O:3])[CH3:2])[CH:37]=[CH2:36]

Participants

7

Reactant 4

HCID 7628Boric AcidHCID 7841Allyl bromideHCID 14797Potassium Hydroxide2×HCID 111153265-Acetamido-N,N'-bis(2,3-dihydroxypropyl)-2,4,6-triiodoisophthalamide

Product 1

HCID 596228935-(N-allylacetamido)-N1,N3-bis(2,3-dihydroxypropyl)-2,4,6-triiodoisophthalamide

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a stirred solution of 5-acetamido-N1,N3-bis(2,3-dihydroxypropyl)-2,4,6-triiodoisophthalamide (7.5 g, 10 mmol) and boric acid (1.24 g, 20 mmol) in water (10 ml) and methanol (7 ml) is added potassium hydroxide (10 M) drop wise until a stable pH 12.5 is established. Allylbromide (860 ul, 10 mmol) is added and potassium hydroxide (10 M) is continuously added to maintain pH 12.5. for 3 h and the mixture is then left stirring over night. The following day the mixture is reduced in vacuo to remove methanol, the resulting aqueous phase is diluted with 50 ml water and treated with acidic and basic ion exchanger. Resins are removed and rinsed and the combined aqueous volume is reduced to dryness in vacuo to yield 5-(N-allylacetamido)-N1,N3-bis(2,3-dihydroxypropyl)-2,4,6-triiodoisophthalamide.

Workup

  1. temperatureto maintain pH 12.5
  2. waitthe mixture is then left
  3. customto remove methanol
  4. additionthe resulting aqueous phase is diluted with 50 ml water
  5. additiontreated with acidic and basic ion exchanger
  6. customResins are removed
  7. washrinsed

Sources & evidence

ORD record
ord-9817ee3996d447b9978d3ebc43a01a3e
Source dataset
uspto-grants-2014_12
Patent number
US08920780B2

Linked notes

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