Ethylene Glycol → HCID 53637418, compound

HRID 257508Notes

Reaction equation

HRID 257508 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]2[CH:6]=[CH:7][C:8]([C:10]3[N:14]([CH2:15][C:16]([OH:18])=[O:17])[N:13]=[N:12][N:11]=3)=[CH:9][C:2]1=2.S(=O)(=O)(O)O.[CH2:24](O)[CH2:25][OH:26]>>[OH:26][CH2:25][CH2:24][O:17][C:16](=[O:18])[CH2:15][N:14]1[C:10]([C:8]2[CH:7]=[CH:6][C:3]3[CH:4]=[CH:5][S:1][C:2]=3[CH:9]=2)=[N:11][N:12]=[N:13]1

Participants

4

Reactant 3

HCID 174Ethylene GlycolHCID 1118Sulfuric AcidHCID 19783458HCID 19783458, compound

Product 1

HCID 53637418HCID 53637418, compoundYield 85.5%

Conditions

Temperature
90 °C

Procedure

To a solution of 400 mg (1.54 mM) of [5-(6-benzo[b]thienyl)tetrazol-1-yl] acetic acid in 3 ml of ethylene glycol was added 0.3 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 400 mg (yield 85.5%) of [5-(6-benzo[b]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-2bda8f3f0c4b4a038a566b0189770f80
Source dataset
uspto-grants-1993_11
Patent number
US05262433

Reaction notes

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