Acetic Anhydride → N-(3-(2-chlorophenyl)-1-methyl-1H-pyrazol-5-yl)acetamide

HRID 1775509Notes

Reaction equation

HRID 1775509 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:12]=[C:11]([NH2:13])[N:10]([CH3:14])[N:9]=1.[C:15](OC(=O)C)(=[O:17])[CH3:16]>N1C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:12]=[C:11]([NH:13][C:15](=[O:17])[CH3:16])[N:10]([CH3:14])[N:9]=1

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 209834423-Amoino-5-(2-chlorophenyl)-2-methylpyrazole

Product 1

HCID 70983638N-(3-(2-chlorophenyl)-1-methyl-1H-pyrazol-5-yl)acetamideYield 70.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 3-(2-chlorophenyl)-1-methyl-1H-pyrazol-5-amine (617 mg, 3 mmol) in pyridine (6 mL) was added acetic anhydride (425 μl, 4.5 mmol). The reaction was stirred at room temperature for 16 h. The mixture was concentrated in vacuo. The crude residue was purified by column chromatography (silica gel, gradient 0 to 100% ethyl acetate/isohexane) yielding N-(3-(2-chlorophenyl)-1-methyl-1H-pyrazol-5-yl)acetamide as a solid (526 mg).

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customThe crude residue was purified by column chromatography (silica gel, gradient 0 to 100% ethyl acetate/isohexane)

Sources & evidence

ORD record
ord-206e264e4eb04f90bc6aa948eecba0aa
Source dataset
uspto-grants-2016_02
Patent number
US09260381B2

Reaction notes

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