Propylene Glycol → HCID 15676653, compound

HRID 1974463Notes

Reaction equation

HRID 1974463 reaction equation
[CH:1]([C:3]1[CH:4]=[N:5][C:6]([C:12]2[NH:13][C:14](=[O:21])[C:15]([CH:18]([CH3:20])[CH3:19])([CH3:17])[N:16]=2)=[C:7]([CH:11]=1)[C:8]([OH:10])=[O:9])=[O:2].[CH2:22]([OH:26])[CH:23](O)[CH3:24].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH3:24][CH:23]1[CH2:22][O:26][CH:1]([C:3]2[CH:4]=[N:5][C:6]([C:12]3[NH:13][C:14](=[O:21])[C:15]([CH:18]([CH3:19])[CH3:20])([CH3:17])[N:16]=3)=[C:7]([CH:11]=2)[C:8]([OH:10])=[O:9])[O:2]1

Participants

5

Reactant 3

HCID 1030Propylene GlycolHCID 6101p-Toluenesulfonic acidHCID 15676631HCID 15676631, compound

Product 1

HCID 15676653HCID 15676653, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 5-formyl-2-(4-isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl)nicotinic acid, 5-(dimethyl acetal) (0.65 g, 0.00194 mol), 1,2-propanediol (0.65 g, 0.0085 mol) and a catalytic amount of p-toluenesulfonic acid in toluene is heated at reflux temperature for 2 hours. The reaction mixture is cooled to room temperature, concentrated in vacuo and the residue is dissolved in methylene chloride. The methylene chloride solution is washed sequentially with water and brine, dried over anhydrous magnesium sulfate and concentrated in vacuo to give a solid. The solid is chromatographed using silica gel and a gradient elution of 100% methylene chloride to 5% methanol in methylene chloride to yield the title compound as a yellow solid (0.5 g, 74%), mp 50°-62° C., identified by IR and NMR spectral analyses.

Workup

  1. temperatureat reflux temperature for 2 hours
  2. concentrationconcentrated in vacuo
  3. dissolutionthe residue is dissolved in methylene chloride
  4. washThe methylene chloride solution is washed sequentially with water and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customto give a solid
  8. customThe solid is chromatographed
  9. washa gradient elution of 100% methylene chloride to 5% methanol in methylene chloride

Sources & evidence

ORD record
ord-8828825195cb47fc982ed791c2b2f4bc
Source dataset
uspto-grants-1994_02
Patent number
US05283230

Reaction notes

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