Methanol → HCID 178498883, compound

HRID 1526936Notes

Reaction equation

HRID 1526936 reaction equation
[CH3:1][C:2]1[C:6]([C:7]([OH:9])=[O:8])=[CH:5][NH:4][N:3]=1.S(Cl)(Cl)=O.[CH3:14]O>>[CH3:1][C:2]1[C:6]([C:7]([O:9][CH3:14])=[O:8])=[CH:5][NH:4][N:3]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 5576005-methyl-1H-pyrazole-4-carboxylic acid

Product 1

HCID 178498883HCID 178498883, compoundYield 57%

Procedure

To a solution of 3-methyl-1H-pyrazole-4-carboxylic acid (1.26 g, 10 mmol) in methanol (100 mL) was added thionyl chloride (5.73 g, 48 mmol) at 0° C. The mixture was stirred for 12 hours. The solvent was evaporated in vacuo. To the residue, saturated sodium bicarbonate aqueous solution was added and the mixture was extracted with ethyl acetate (100 mL×3). The organic phases were combined, dried over sodium sulfate, filtered and concentrated in vacuo to give methyl 3-methyl-1H-pyrazole-4-carboxylate (0.8 g, 57%). 1H NMR (300 MHz, CDCl3): δ 7.87 (s, 1H), 3.84 (s, 3H), 2.53 (s, 3H).

Workup

  1. customThe solvent was evaporated in vacuo
  2. additionTo the residue, saturated sodium bicarbonate aqueous solution was added
  3. extractionthe mixture was extracted with ethyl acetate (100 mL×3)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e4e5599f58194dd5b858f1ccc8c936e6
Source dataset
uspto-grants-2015_07
Patent number
US09085583B2

Reaction notes

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