Sulfuric Acid → HCID 54264503, compound

HRID 2228917Notes

Reaction equation

HRID 2228917 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([CH:7]=[CH:8][C:9]([OH:11])=[O:10])[CH:4]=[N:3]1.S(=O)(=O)(O)O.[C:17](=O)([O-])[O-].[Na+].[Na+]>CO>[CH3:1][N:2]1[CH:6]=[C:5]([CH:7]=[CH:8][C:9]([O:11][CH3:17])=[O:10])[CH:4]=[N:3]1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 10340Sodium CarbonateHCID 592440HCID 592440, compound

Product 1

HCID 54264503HCID 54264503, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3-(1-Methylpyrazol-4-yl)acrylic acid (18.86 g) was added to a solution of sulphuric acid (15 ml) in methanol (150 ml), and the mixture refluxed for 2 hours, cooled, and poured onto ice. The acid was neutralised with solid sodium carbonate and the product extracted into dichloromethane, which was dried and evaporated. Crystallisation from ether/petrol gave methyl 3-(1-methylpyrazol-4-yl)acrylate (16.0 g). 1H-NMR (d6-DMSO) δ 3.77 (3H, s), 3.91 (3H, s), 6.16 (1H, d), 7.54 (1H, s), 7.56 (1H, d), 7.69 (1H, s). (APCI) M+H=167. C8H10N2O2 requires 166.

Workup

  1. temperaturethe mixture refluxed for 2 hours
  2. temperaturecooled
  3. additionpoured onto ice
  4. extractionthe product extracted into dichloromethane, which
  5. customwas dried
  6. customevaporated
  7. customCrystallisation from ether/petrol

Sources & evidence

ORD record
ord-2b777a701ca74943afa336f7d195e6e4
Source dataset
uspto-grants-2002_07
Patent number
US06417192B1

Reaction notes

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