Acetic Acid → tert-Butyl 3-(3,5-dichlorophenyl)-1H-pyrazole-5-carboxylate

HRID 1865413Notes

Reaction equation

HRID 1865413 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9](=O)[CH2:10][C:11](=O)[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH:5]=[C:6]([Cl:8])[CH:7]=1.[NH2:21][NH2:22].C(O)(=O)C>C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:10]=[C:11]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[NH:22][N:21]=2)[CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 9321HydrazineHCID 67487680HCID 67487680, compound

Product 1

HCID 86620042tert-Butyl 3-(3,5-dichlorophenyl)-1H-pyrazole-5-carboxylate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of the product from step C (6.8 g, 21.7 mmol) in 125 mL of ethanol was added hydrazine (0.75 mL, 23.9 mmol) and 10 mL of glacial acetic acid. The reaction mixture was stirred at ambient temperature for 16 h then was concentrated in vacuo and the residue suspended in ethyl acetate. The organic layer was washed successively with two portions of saturated aqueous sodium bicarbonate solution and one portion of brine. The organic layer was dried over magnesium sulfate, and concentrated in vacuo to provide the title compound as a pale yellow solid which was used without further purification.

Workup

  1. concentrationthen was concentrated in vacuo
  2. washThe organic layer was washed successively with two portions of saturated aqueous sodium bicarbonate solution and one portion of brine
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ce6f14ea0c324ff181cd33339185a23c
Source dataset
uspto-grants-2009_12
Patent number
US07625938B2

Reaction notes

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