Dimethylacetamide → 3-[N-(2,3-dihydroxypropyl)carbamoyl]-5-[N-(2,3-dihydroxypropyl)-N-methylcarbamoyl]-2,4,6-triiodobenzonitrile

HRID 1065064Notes

Reaction equation

HRID 1065064 reaction equation
[C:1]([C:3]1[C:4]([I:22])=[C:5]([C:14](=[O:21])[NH:15][CH2:16][CH:17]([OH:20])[CH2:18][OH:19])[C:6]([I:13])=[C:7]([C:11]=1[I:12])[C:8](Cl)=[O:9])#[N:2].C[NH:24][CH2:25][CH:26]([OH:29])[CH2:27][OH:28].[CH3:30]C(N(C)C)=O>>[OH:29][CH:26]([CH2:27][OH:28])[CH2:25][NH:24][C:8]([C:7]1[C:11]([I:12])=[C:3]([C:4]([I:22])=[C:5]([C:14](=[O:21])[N:15]([CH2:16][CH:17]([OH:20])[CH2:18][OH:19])[CH3:30])[C:6]=1[I:13])[C:1]#[N:2])=[O:9]

Participants

4

Reactant 3

HCID 31374DimethylacetamideHCID 27341223-(Methylamino)propane-1,2-diolHCID 129408505-Cyano-3-[N-(2,3-dihydroxypropyl)carbamoyl]-2,4,6-triiodobenzoyl chloride

Product 1

HCID 129408523-[N-(2,3-dihydroxypropyl)carbamoyl]-5-[N-(2,3-dihydroxypropyl)-N-methylcarbamoyl]-2,4,6-triiodobenzonitrileYield 81%

Procedure

6.6 g of 5-cyano-3-[N-(2,3-dihydroxypropyl)carbamoyl]-2,4,6-triiodobenzoic acid chloride is dissolved in 40 ml of dimethylacetamide and combined with 2.3 g of N-methylamino-2,3-propanediol. The mixture is stirred for one hour at room temperature and then concentrated under vacuum. The thus-obtained crude product can be used directly for nitrile saponification. To isolate the pure product the dilute aqueous solution of the crude product is treated with a cation exchange resin and an anion exchange resin, and the filtered solution is concentrated under vacuum to dryness, thus obtaining 5.9 g (81% of theory) of 3-[N-(2,3-dihydroxypropyl)carbamoyl]-5-[N-(2,3-dihydroxypropyl)-N-methylcarbamoyl]-2,4,6-triiodobenzonitrile; mp 215° C.

Workup

  1. concentrationconcentrated under vacuum
  2. customThe thus-obtained crude product
  3. customTo isolate the pure product the dilute aqueous solution of the crude product
  4. additionis treated with a cation exchange resin
  5. concentrationan anion exchange resin, and the filtered solution is concentrated under vacuum to dryness

Sources & evidence

ORD record
ord-5a1d3feb1132419d9119b42134f81a8a
Source dataset
uspto-grants-1982_05
Patent number
US04328202

Reaction notes

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