Benzene → HCID 18958045, compound

HRID 2379197Notes

Reaction equation

HRID 2379197 reaction equation
NC(N)=[O:3].C([N:7]([CH2:10][CH3:11])CC)C.[F:12][C:13]1[C:18]([C:19](Cl)=[O:20])=[C:17]([F:22])[C:16]([F:23])=[C:15]([F:24])[C:14]=1[F:25].Cl.[CH:27]1[CH:32]=CC=C[CH:28]=1>C(OCC)(=O)C>[F:12][C:13]1[C:18]([C:19]([NH:7][CH2:10][CH2:11][CH2:28][C:27](=[O:3])[CH3:32])=[O:20])=[C:17]([F:22])[C:16]([F:23])=[C:15]([F:24])[C:14]=1[F:25]

Participants

7

Reactant 5

HCID 241BenzeneHCID 313Hydrochloric AcidHCID 1176UreaHCID 8471TriethylamineHCID 75256Pentafluorobenzoyl chloride

Product 1

HCID 18958045HCID 18958045, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

The preceding amino-ketone (1.03 g, 10 mmol) was dissolved in dry benzene (20 mL). Triethylamine (1.5 mL) was added. Pentafluorobenzoyl chloride (2.31 g, 10 mmol) was added dropwise with stirring over 10 min. The reaction mixture was stirred at room temperature for 30 min, and then acidified with 10% HCl. Ethyl acetate was added, and the organic layer washed with 10% NaHCO3, H2O, and dried over anhydrous Na2SO4. Evaporation of the solvent afforded a yellow oil which was purified by flash column chromatography (3:7 ethyl acetate/hexane) to give white crystals (1.65 g, 55%),

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 30 min
  2. washthe organic layer washed with 10% NaHCO3, H2O
  3. dry with materialdried over anhydrous Na2SO4
  4. customEvaporation of the solvent
  5. customafforded a yellow oil which
  6. customwas purified by flash column chromatography (3:7 ethyl acetate/hexane)

Sources & evidence

ORD record
ord-3ffcb32305d74294aabc9ddbd4d14517
Source dataset
uspto-grants-1994_11
Patent number
US05360819

Reaction notes

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