3-Chloro-1,2-propanediol → HCID 12940854, compound

HRID 728005Notes

Reaction equation

HRID 728005 reaction equation
[CH3:1][NH:2][C:3](=[O:18])[C:4]1[C:12]([I:13])=[C:11]([C:14]#[N:15])[C:10]([I:16])=[C:6]([C:7]([OH:9])=[O:8])[C:5]=1[I:17].C(=O)([O-])[O-].[Na+].[Na+].Cl[CH2:26][CH:27]([OH:30])[CH2:28][OH:29]>CN(C)C=O>[OH:30][CH:27]([CH2:28][OH:29])[CH2:26][O:8][C:7](=[O:9])[C:6]1[C:10]([I:16])=[C:11]([C:14]#[N:15])[C:12]([I:13])=[C:4]([C:3](=[O:18])[NH:2][CH3:1])[C:5]=1[I:17]

Participants

5

Reactant 3

HCID 72903-Chloro-1,2-propanediolHCID 10340Sodium CarbonateHCID 12940824HCID 12940824, compound

Product 1

HCID 12940854HCID 12940854, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

60 g 5-cyano-2,4,6-triiodoisophthalic acid monomethylamide is heated in 150 ml of dimethylformamide with 22 g of sodium carbonate (anhydrous) and 28 g of 1-chloro-2,3-propanediol for 4 hours to 90° C. The mixture is then cooled, vacuum-filtered from the precipitated sodium chloride, and concentrated to dryness under vacuum. The residue is dissolved in 250 ml of ethyl acetate, the solution is filtered over active carbon, and the filtrate is concentrated to half its volume. The product is cooled in an ice bath and gently combined with such an amount of diisopropyl ether that crystallization sets in. After stirring for several, hours in an ice bath, the crystallized product is vacuum-filtered, washed with diisopropyl ether, and dried at 50° C., thus obtaining 48.5 g (=74% of theory) of 5-cyano-3-methylcarbamoyl-2,4,6-triiodobenzoic acid (2,3-dihydroxypropyl)ester as a white powder, mp 117-120° C.

Workup

  1. temperatureThe mixture is then cooled
  2. filtrationvacuum-filtered from the precipitated sodium chloride
  3. concentrationconcentrated to dryness under vacuum
  4. dissolutionThe residue is dissolved in 250 ml of ethyl acetate
  5. filtrationthe solution is filtered over active carbon
  6. concentrationthe filtrate is concentrated to half its volume
  7. temperatureThe product is cooled in an ice bath
  8. customthat crystallization sets in
  9. filtrationthe crystallized product is vacuum-filtered
  10. washwashed with diisopropyl ether
  11. customdried at 50° C.

Sources & evidence

ORD record
ord-08f7c160ed76454a9e463c35a4e7e7fb
Source dataset
uspto-grants-1991_09
Patent number
US05047228

Reaction notes

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