Ethylene Glycol → HCID 54524012, compound

HRID 257498Notes

Reaction equation

HRID 257498 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[N:10]([CH2:11][C:12]([OH:14])=[O:13])[N:9]=[N:8][N:7]=1.S(=O)(=O)(O)O.[CH2:20](O)[CH2:21][OH:22]>>[OH:22][CH2:21][CH2:20][O:13][C:12](=[O:14])[CH2:11][N:10]1[C:6]([C:2]2[S:1][CH:5]=[CH:4][CH:3]=2)=[N:7][N:8]=[N:9]1

Participants

4

Reactant 3

HCID 174Ethylene GlycolHCID 1118Sulfuric AcidHCID 2159421H-Tetrazole-1-acetic acid, 5-(2-thienyl)-

Product 1

HCID 54524012HCID 54524012, compoundYield 88.5%

Conditions

Temperature
90 °C

Procedure

To a solution of a 1 g (4.7 mM) of [5-(2-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 1 g (yield 88.5%) of [5-(2-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-e1dc088cfc2649cb98c60310af1e22ba
Source dataset
uspto-grants-1993_11
Patent number
US05262433

Reaction notes

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