Ethanol → HCID 178469911, compound

HRID 1094792Notes

Reaction equation

HRID 1094792 reaction equation
[CH3:1][C:2]1[C:6]([C:7]([OH:9])=[O:8])=[CH:5][NH:4][N:3]=1.S(=O)(=O)(O)O.C([O-])(O)=O.[Na+].[CH2:20](O)[CH3:21]>>[CH3:1][C:2]1[C:6]([C:7]([O:9][CH2:20][CH3:21])=[O:8])=[CH:5][NH:4][N:3]=1

Participants

5

Reactant 4

HCID 702EthanolHCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 5576005-methyl-1H-pyrazole-4-carboxylic acid

Product 1

HCID 178469911HCID 178469911, compoundYield 58%

Procedure

To a solution of 3-methyl-1H-pyrazole-4-carboxylic acid (2.986 g, 23.68 mmol) in ethanol (20 ml) was added concentrated sulphuric acid (1 ml). The reaction was heated at reflux for 6 hours, cooled to room temperature, and then poured into a saturated aqueous solution of NaHCO3. The mixture was extracted with dichloromethane (3×50 ml) then the combined organic extracts dried over MgSO4 and concentrated in vacuo. The product crystallised on standing (2.105 g, 58% yield).

Workup

  1. temperatureThe reaction was heated
  2. temperatureat reflux for 6 hours
  3. extractionThe mixture was extracted with dichloromethane (3×50 ml)
  4. dry with materialthe combined organic extracts dried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe product crystallised

Sources & evidence

ORD record
ord-1674b5606b7f453484b814b71dcaa79e
Source dataset
uspto-grants-2012_03
Patent number
US08134007B2

Reaction notes

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