Acetic Anhydride → HCID 10619341, compound

HRID 654794Notes

Reaction equation

HRID 654794 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([C:13]3[CH:18]=[CH:17][C:16]([S:19]([CH3:22])(=[O:21])=[O:20])=[CH:15][CH:14]=3)=[CH:11][C:10]([NH2:23])=[N:9]2)=[CH:4][CH:3]=1.[C:24](OC(=O)C)(=[O:26])[CH3:25]>ClCCl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:12]([C:13]3[CH:18]=[CH:17][C:16]([S:19]([CH3:22])(=[O:21])=[O:20])=[CH:15][CH:14]=3)=[CH:11][C:10]([NH:23][C:24](=[O:26])[CH3:25])=[N:9]2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 10782725HCID 10782725, compound

Product 1

HCID 10619341HCID 10619341, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 1-(4-fluorophenyl)-5-[4-(methylsulfonyl)phenyl]pyrazol-3-amine (0.7 g) and acetic anhydride (0.22 ml) in dichloromethane (15 ml) was stirred at ambient temperature for 3 hours, and concentrated. The residue was purified by column chromatography on silica gel (15 g) eluting with a mixture of toluene and ethyl acetate (2:1). The desired product (0.63 g) was recrystallized from ethanol to give pale brown crystals of N-{1-(4-fluorophenyl)-5-[4-(methylsulfonyl)phenyl]-3-pyrazolyl}acetamide (0.52 g).

Workup

  1. concentrationconcentrated
  2. customThe residue was purified by column chromatography on silica gel (15 g)
  3. washeluting with a mixture of toluene and ethyl acetate (2:1)
  4. customThe desired product (0.63 g) was recrystallized from ethanol

Sources & evidence

ORD record
ord-76af8b58c0754665bc04f4ed11e8822c
Source dataset
uspto-grants-1992_07
Patent number
US05134142

Reaction notes

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