Ethylene Glycol → HCID 53839625, compound

HRID 257497Notes

Reaction equation

HRID 257497 reaction equation
[CH3:1][S:2][C:3]1[S:4][CH:5]=[CH:6][C:7]=1[C:8]1[N:12]([CH2:13][C:14]([OH:16])=[O:15])[N:11]=[N:10][N:9]=1.S(=O)(=O)(O)O.[CH2:22](O)[CH2:23][OH:24]>>[OH:24][CH2:23][CH2:22][O:15][C:14](=[O:16])[CH2:13][N:12]1[C:8]([C:7]2[CH:6]=[CH:5][S:4][C:3]=2[S:2][CH3:1])=[N:9][N:10]=[N:11]1

Participants

4

Reactant 3

HCID 174Ethylene GlycolHCID 1118Sulfuric AcidHCID 19427381HCID 19427381, compound

Product 1

HCID 53839625HCID 53839625, compoundYield 88.1%

Conditions

Temperature
90 °C

Procedure

To a solution of 920 mg (3.6 mM) of [5-(2-methylthio-3-thienyl)tetrazol-1-yl]acetic acid in 5 ml of ethylene glycol was added 0.5 ml of sulfuric acid. After the addition, the mixture was stirred at 90° C. for 2.5 hrs. The mixture was then poured into ice-water and extracted with ethyl acetate. The organic phase was washed with water, dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The resultant residue was subjected to silica gel column chromatography (eluent: chloroform/methyl alcohol=50/1) for separation and purification, to give 950 mg (yield 88.1%) of [5-(2-methylthio-3-thienyl)tetrazol-1-yl] acetic acid 2-hydroxyethyl ester.

Workup

  1. additionAfter the addition
  2. extractionextracted with ethyl acetate
  3. washThe organic phase was washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe resultant residue was subjected to silica gel column chromatography (eluent: chloroform/methyl alcohol=50/1) for separation and purification

Sources & evidence

ORD record
ord-47468e279be640f0ba8208b697c7a950
Source dataset
uspto-grants-1993_11
Patent number
US05262433

Reaction notes

Loading…