Diisopropylamine → N-Propenyl-4-trifluoromethoxy-benzamide

HRID 842930Notes

Reaction equation

HRID 842930 reaction equation
C(NC(C)C)(C)C.[CH2:8]([NH:11][C:12](=[O:24])[C:13]1[CH:18]=[CH:17][C:16]([O:19][C:20]([F:23])([F:22])[F:21])=[CH:15][CH:14]=1)[CH:9]=[CH2:10]>C1COCC1>[CH:8]([NH:11][C:12](=[O:24])[C:13]1[CH:14]=[CH:15][C:16]([O:19][C:20]([F:22])([F:23])[F:21])=[CH:17][CH:18]=1)=[CH:9][CH3:10]

Participants

4

Reactant 2

HCID 7912DiisopropylamineHCID 22616308HCID 22616308, compound

Product 1

HCID 54407387N-Propenyl-4-trifluoromethoxy-benzamideYield 85%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of diisopropylamine (6.3 mL, 45 mmol) in THF 100 mL at −78° C., was added n-butyllithilum (18 mL, 45 mmol of a 2.5M solution in hexanes). After 10 min. a solution (10 mL THF) of N-Allyl-4-trifluoromethoxy-benzamide 11 (5 g, 20 mmol) was added dropwise to the reaction mixture. The resulting dark blue reaction mixture was allowed to warm to 0° C. where it was quenched by addition of aqueous ammonium chloride. Ether was added and the organic layer was separated, dried (sodium sulfate), and concentrated. The residue was purified by silica gel chromatography (20% ether/hexanes) to provide the title compound (colorless solid 85%). 1H NMR (400 MHz, CDCl3) δ7.85 (d, J=8.8 Hz, 2 H, Ar), 7.55 (s, 1 H, NH), 7.29 (d, J=9.5 Hz, 2 H, Ar), 6.95 (m, 1 H, NHCHCH), 5.35 & 4.99 (m, 1 H, CHCHCH3), 1.72 (m, 3 H, CH3)

Workup

  1. customThe resulting dark blue reaction mixture
  2. customwas quenched by addition of aqueous ammonium chloride
  3. additionEther was added
  4. customthe organic layer was separated
  5. dry with materialdried (sodium sulfate)
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel chromatography (20% ether/hexanes)

Sources & evidence

ORD record
ord-673a0ee6aa4e4d178e0ea7de968979b6
Source dataset
uspto-grants-2002_04
Patent number
US06376530B1

Reaction notes

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