Acetic Anhydride → ethyl 2-(5-acetamido-3-phenyl-1H-pyrazol-1-yl)acetate

HRID 2205823Notes

Reaction equation

HRID 2205823 reaction equation
[C:1](OC(=O)C)(=[O:3])[CH3:2].[NH2:8][C:9]1[N:13]([CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])[N:12]=[C:11]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:10]=1>N1C=CC=CC=1>[C:1]([NH:8][C:9]1[N:13]([CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])[N:12]=[C:11]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:10]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 820314ethyl 2-(5-amino-3-phenyl-1H-pyrazol-1-yl)acetate

Product 1

HCID 86717316ethyl 2-(5-acetamido-3-phenyl-1H-pyrazol-1-yl)acetateYield 94.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Acetic anhydride (12.7 mL, 134.8 mmol) was added dropwise to a solution of ethyl 2-(5-amino-3-phenyl-pyrazol-1-yl)acetate (31.5 g, 128.4 mmol) in pyridine (200 mL) at 0° C. under an atmosphere of nitrogen. Upon complete addition, the reaction mixture was warmed to room temperature and stirred for 16 h. The reaction mixture was concentrated in vacuo. The residue was diluted in CH2Cl2 (250 mL). The organic phase was washed with water and brine, dried (MgSO4), filtered and concentrated in vacuo. The residue was triturated from diethyl ether, filtered and dried to provide the title compound as a white solid (34.81 g).

Workup

  1. additionUpon complete addition
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. additionThe residue was diluted in CH2Cl2 (250 mL)
  4. washThe organic phase was washed with water and brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was triturated from diethyl ether
  9. filtrationfiltered
  10. customdried

Sources & evidence

ORD record
ord-dc18988fdc3d4e5d95e383b47fb1d6a5
Source dataset
uspto-grants-2016_06
Patent number
US09371332B2

Reaction notes

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