Sulfuric Acid → HCID 9817233, compound

HRID 277007Notes

Reaction equation

HRID 277007 reaction equation
[CH2:1]([C:3]1[C:7]([C:8]2[O:12][N:11]=[CH:10][C:9]=2[CH3:13])=[C:6]([S:14][CH3:15])[S:5][C:4]=1[C:16]#[N:17])[CH3:2].S(=O)(=O)(O)[OH:19]>>[CH2:1]([C:3]1[C:7]([C:8]2[O:12][N:11]=[CH:10][C:9]=2[CH3:13])=[C:6]([S:14][CH3:15])[S:5][C:4]=1[C:16]([NH2:17])=[O:19])[CH3:2]

Participants

3

Reactant 2

HCID 1118Sulfuric AcidHCID 15513025HCID 15513025, compound

Product 1

HCID 9817233HCID 9817233, compoundYield 42%

Conditions

Temperature
60 °C

Procedure

To 3-ethyl-4-(4-methylisoxazol-5-yl)-5-(methylthio)thiophene-2-carbonitrile (0.87 g, 3.3 mmol) was added conc. sulfuric acid (11 ml) and the mixture was heated at 60° C. for 1.5 hours. The reaction solution was allowed to cool down to room temperature, ice was added and then the mixture was extracted with ethyl acetate. The organic layer was washed (with water, saturated aqueous sodium hydrogen-carbonate and saturated aqueous sodium chloride, in turn), dried (over anhydrous magnesium sulfate) and concentrated under reduced pressure. The residue thus obtained was purified by silica gel column chromatography (developing solvent: chloroform/ ethyl acetate=1:0-3:1) and recrystallized from diethyl ether to afford 3-ethyl-4-(4-methylisoxazol-5-yl)-5-(methylthio)thiophene-2-carboxamide (0.39 g, 42%) as colorless crystals.

Workup

  1. temperatureto cool down to room temperature
  2. additionice was added
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed (with water, saturated aqueous sodium hydrogen-carbonate and saturated aqueous sodium chloride, in turn)
  5. dry with materialdried (over anhydrous magnesium sulfate)
  6. concentrationconcentrated under reduced pressure
  7. customThe residue thus obtained
  8. customwas purified by silica gel column chromatography (developing solvent: chloroform/ ethyl acetate=1:0-3:1)
  9. customrecrystallized from diethyl ether

Sources & evidence

ORD record
ord-de31b2d3d2264a588e21481a39628bde
Source dataset
uspto-grants-2002_03
Patent number
US06355663B1

Reaction notes

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