Ethanol → 1-[(4-Methoxy)phenyl]-3-(ethoxycarbonyl)-5-(methoxycarbonyl)pyrazole

HRID 610141Notes

Reaction equation

HRID 610141 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:13]([C:14]([O:16][CH3:17])=[O:15])=[CH:12][C:11]([C:18]([OH:20])=[O:19])=[N:10]2)=[CH:5][CH:4]=1.[CH:21](N(C(C)C)CC)(C)[CH3:22].C(O)C>S(Cl)(Cl)=O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:13]([C:14]([O:16][CH3:17])=[O:15])=[CH:12][C:11]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[N:10]2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 81531DiisopropylethylamineHCID 542100671-[(4-Methoxy)phenyl]-5-(methoxycarbonyl)pyrazole-3-carboxylic acid

Product 1

HCID 544294771-[(4-Methoxy)phenyl]-3-(ethoxycarbonyl)-5-(methoxycarbonyl)pyrazoleYield 45%

Reagents, catalysts & solvents 1

HCID 24386Thionyl ChlorideSolvent

Procedure

A solution of 1-[(4-methoxy)phenyl]-5-(methoxycarbonyl)pyrazole -3-carboxylic acid (7.50 g, 27.1 mmol) in 50 mL of thionyl chloride was stirred at 80° C. for 1 h. The volatiles were then removed and the residue was azeotroped with 20 mL of toluene and dried in vacuo. The residue was dissolved in 100 mL of tetrahydrofuran and then there was added diisopropylethylamine (11.8 mL, 67.9 mmol) and absolute ethanol (3.2 mL, 54.3 mmol). The reaction mixture was allowed to stir at ambient temperature for 24 h. The volatiles were removed and the residue was dissolved in ethyl acetate. This solution was filtered through a pad of silica gel and was concentrated in vacuo to afford 3.7 g (45%) of the title compound which was used without purification. LRMS (DCI): 305.1 (M+H)+.

Workup

  1. customThe volatiles were then removed
  2. customthe residue was azeotroped with 20 mL of toluene
  3. customdried in vacuo
  4. dissolutionThe residue was dissolved in 100 mL of tetrahydrofuran
  5. customThe volatiles were removed
  6. dissolutionthe residue was dissolved in ethyl acetate
  7. filtrationThis solution was filtered through a pad of silica gel
  8. concentrationwas concentrated in vacuo

Sources & evidence

ORD record
ord-61ddf471416d4863a7025f3b59489ee6
Source dataset
uspto-grants-1999_12
Patent number
US05998424

Reaction notes

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