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

HRID 1525377Notes

Reaction equation

HRID 1525377 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-19630ce319d44db0b23aaa711fbefe8b
Source dataset
uspto-grants-2015_07
Patent number
US09079909B2

Reaction notes

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