Methanol → methyl 1H-thieno[3,2-c]pyrazole-5-carboxylate

HRID 876780Notes

Reaction equation

HRID 876780 reaction equation
[NH:1]1[C:5]2[CH:6]=[C:7]([C:9]([OH:11])=[O:10])[S:8][C:4]=2[CH:3]=[N:2]1.OS(O)(=O)=O.[CH3:17]O>>[NH:1]1[C:5]2[CH:6]=[C:7]([C:9]([O:11][CH3:17])=[O:10])[S:8][C:4]=2[CH:3]=[N:2]1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 596408271H-thieno[3,2-c]pyrazole-5-carboxylic acid

Product 1

HCID 68289363methyl 1H-thieno[3,2-c]pyrazole-5-carboxylate

Procedure

To a solution of 1H-thieno[3,2-c]pyrazole-5-carboxylic acid (G-1) (3.0 g, 17.9 mmol) in MeOH (50 mL) was added concentrated H2SO4 (0.3 mL). The reaction mixture was stirred at reflux for 60 h. Solvent was removed in vacuo. Ethyl acetate was added to dilute the mixture. The mixture was washed with aqueous NaHCO3 solution, dried over Na2SO4, and concentrated in vacuo to afford the title compound (2.4 g).

Workup

  1. temperatureat reflux for 60 h
  2. customSolvent was removed in vacuo
  3. additionEthyl acetate was added
  4. additionto dilute the mixture
  5. washThe mixture was washed with aqueous NaHCO3 solution
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8be39d256262487db282304e7cb75cb7
Source dataset
uspto-grants-2015_03
Patent number
US08987269B2

Reaction notes

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