Sodium Hydroxide → 3-(1-methyl-1H-1,2,3-triazol-4-yl)prop-2-enoic acid

HRID 1979019Notes

Reaction equation

HRID 1979019 reaction equation
[OH-].[Na+].C[O:4][C:5](=[O:14])/[CH:6]=[CH:7]/[C:8]1[N:9]=[N:10][N:11]([CH3:13])[CH:12]=1>>[CH3:13][N:11]1[CH:12]=[C:8](/[CH:7]=[CH:6]/[C:5]([OH:14])=[O:4])[N:9]=[N:10]1

Participants

3

Reactant 2

HCID 14798Sodium Hydroxide2×HCID 21202730Methyl-(E)-3-(1-methyl-1,2,3-triazol-4-yl)acrylate

Product 1

HCID 212027733-(1-methyl-1H-1,2,3-triazol-4-yl)prop-2-enoic acidYield 25.5%

Procedure

10% Sodium hydroxide solution (3 ml) was added to a solution of the product from step 1 (3.2 g). The mixture was stirred at room temperature for 15 hours, further 10% sodium hydroxide solution (2 ml) added and then heated to reflux for 3 hours. On cooling the reaction mixture was partitioned between ethyl acetate and water. The organics were re-extracted with saturated sodium hydrogen carbonate solution and the combined aqueous extracts acidified to pH 1 with conc. hydrochloric acid. After extraction into ethyl acetate and dying over magnesium sulphate the solvent was removed to afford the title compound, (748 mg); 1H NMR (d6-DMSO) 4.07 (3H, s), 6.53 (1H, d, J 16.0 Hz), 7.53 (1H, d, J 16.0 Hz), 8.44 (1H, s), 12.48 (1H, br).

Workup

  1. temperatureheated
  2. temperatureto reflux for 3 hours
  3. temperatureOn cooling the reaction mixture
  4. customwas partitioned between ethyl acetate and water
  5. extractionThe organics were re-extracted with saturated sodium hydrogen carbonate solution
  6. extractionAfter extraction into ethyl acetate
  7. customwas removed

Sources & evidence

ORD record
ord-3c3367edaee442a6950c67c69a4ba0b7
Source dataset
uspto-grants-2001_05
Patent number
US06239175B1

Reaction notes

Loading…