Sulfuric Acid → HCID 54174452, compound

HRID 257513Notes

Reaction equation

HRID 257513 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]([C:6]2[N:10]([CH2:11][C:12]([OH:14])=[O:13])[N:9]=[N:8][N:7]=2)=[CH:2]1.S(=O)(=O)(O)O.[CH3:20][O:21][CH2:22][CH2:23]O>>[CH3:20][O:21][CH2:22][CH2:23][O:13][C:12](=[O:14])[CH2:11][N:10]1[C:6]([C:3]2[CH:4]=[CH:5][S:1][CH:2]=2)=[N:7][N:8]=[N:9]1

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 80192-MethoxyethanolHCID 3035658(5-(3-Thienyl)tetrazol-1-yl)acetic acid

Product 1

HCID 54174452HCID 54174452, compoundYield 82.3%

Conditions

Temperature
90 °C

Procedure

To a solution of 2 g (9.51 mM) of [5-(3-thienyl)tetrazol-1-yl]acetic acid in 10 ml of 2-methoxyethanol was added 1 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/ethyl alcohol=30/1) for separation and purification, to give 2.1 g (yield 82.3%) of [5-(3-thienyl)tetrazol-1-yl]acetic acid 2-methoxyethyl 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/ethyl alcohol=30/1) for separation and purification

Sources & evidence

ORD record
ord-5381543bf4f3431eb0d15e0b9024050c
Source dataset
uspto-grants-1993_11
Patent number
US05262433

Reaction notes

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