Acetyl chloride → N-(2-acetyl-5-phenyl-pyrazol-3-yl)acetamide

HRID 1615712Notes

Reaction equation

HRID 1615712 reaction equation
[C:1]1([C:7]2[NH:11][N:10]=[C:9]([NH2:12])[CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CN1[CH2:19][CH2:18][O:17]CC1.[C:20](Cl)(=[O:22])[CH3:21]>C(Cl)Cl.O>[C:20]([N:10]1[C:9]([NH:12][C:18](=[O:17])[CH3:19])=[CH:8][C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[N:11]1)(=[O:22])[CH3:21]

Participants

6

Reactant 3

HCID 6367Acetyl chlorideHCID 79724-MethylmorpholineHCID 1366553-Amino-5-phenylpyrazole

Product 1

HCID 86717295N-(2-acetyl-5-phenyl-pyrazol-3-yl)acetamideYield 88.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 5-phenyl-1H-pyrazol-3-amine (18.6 g, 0.117 mol) and N-methylmorpholine (30.8 mL, 0.281 mol) in CH2Cl2 (250 mL) was added acetyl chloride (20 mL, 0.281 mol) dropwise at 0° C. under an atmosphere of nitrogen. The reaction mixture was stirred at room temperature for 3 h. The reaction mixture was diluted with CH2Cl2 and water. The layers were separated and the organic layer was washed with water and brine, dried (phase separator cartridge) and concentrated in vacuo. Diethyl ether was added to the residue and the solid was collected by filtration, yielding the title compound as a solid (25.1 g).

Workup

  1. customThe layers were separated
  2. washthe organic layer was washed with water and brine
  3. customdried (phase separator cartridge)
  4. concentrationconcentrated in vacuo
  5. additionDiethyl ether was added to the residue
  6. filtrationthe solid was collected by filtration

Sources & evidence

ORD record
ord-c0b72b16019348b2933449c32e606293
Source dataset
uspto-grants-2014_07
Patent number
US08765762B2

Reaction notes

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