Ethylene Glycol → HCID 14390430, compound

HRID 2351767Notes

Reaction equation

HRID 2351767 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:16]([C@H:17]([CH3:21])[C:18]([OH:20])=[O:19])[C:11]3=[N:12][CH:13]=[CH:14][CH:15]=[C:10]3[N:9]=2)=[CH:4][CH:3]=1.C(=O)(O)[O-].[Na+].O.[CH2:28](O)[CH2:29][OH:30]>S(=O)(=O)(O)O>[OH:30][CH2:29][CH2:28][O:19][C:18](=[O:20])[C@@H:17]([CH3:21])[N:16]1[C:11]2=[N:12][CH:13]=[CH:14][CH:15]=[C:10]2[N:9]=[C:8]1[C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=1

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 962WaterHCID 516892Sodium BicarbonateHCID 14390428HCID 14390428, compound

Product 1

HCID 14390430HCID 14390430, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidCatalyst

Procedure

A solution of (R)-2(4-chlorophenyl)-α-methyl-3H-imidazo[4,5-b]pyridine-3-acetic acid (4.22 g, 0.014 mole) and concentrated sulfuric acid (4 drops) in ethylene glycol (50 ml) was refluxed under nitrogen for three hours, and then poured into a saturated sodium bicarbonate solution (200 ml). Water (50 ml) was added and the product was extracted into three portions of ethyl acetate. The combined organic layers were washed twice with water and once with a saturated sodium chloride solution, dried over magnesium sulfate, treated with charcoal, filtered, and evaporated under reduced pressure to give 2.6 g (54% yield) of an oily glass. The glass was dissolved in hot isopropyl ether (with a little isopropyl alcohol added), filtered while hot, and cooled to room temperature with stirring, causing a solid to precipitate. The mixture was cooled in the freezer, and the solid was collected by filtration, rinsed with isopropyl ether and dried under high vacuum at room temperature to give 1.60 g of title compound, mp. 110°-113° C.

Workup

  1. extractionthe product was extracted into three portions of ethyl acetate
  2. washThe combined organic layers were washed twice with water and once with a saturated sodium chloride solution
  3. dry with materialdried over magnesium sulfate
  4. additiontreated with charcoal
  5. filtrationfiltered
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-65bf5bafe70f488887c7518c95ac19ae
Source dataset
uspto-grants-1989_10
Patent number
US04873251

Reaction notes

Loading…