Diisopropylamine → 6-bromo-N,N-diisopropyl-2-naphthamide

HRID 1061879Notes

Reaction equation

HRID 1061879 reaction equation
[CH:1]([NH:4][CH:5]([CH3:7])[CH3:6])([CH3:3])[CH3:2].C(N(CC)CC)C.[Br:15][C:16]1[CH:17]=[C:18]2[C:23](=[CH:24][CH:25]=1)[CH:22]=[C:21]([C:26](Cl)=[O:27])[CH:20]=[CH:19]2>C1COCC1>[Br:15][C:16]1[CH:17]=[C:18]2[C:23](=[CH:24][CH:25]=1)[CH:22]=[C:21]([C:26]([N:4]([CH:5]([CH3:7])[CH3:6])[CH:1]([CH3:3])[CH3:2])=[O:27])[CH:20]=[CH:19]2

Participants

5

Reactant 3

HCID 7912DiisopropylamineHCID 8471TriethylamineHCID 218796066-Bromo-2-naphthoyl chloride

Product 1

HCID 218796396-bromo-N,N-diisopropyl-2-naphthamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution (800 mL) of diisopropylamine (112 mL) and triethylamine (112 mL) in THF was added dropwise a solution (400 mL) of 6-bromo-2-naphthoyl chloride in THF under ice-cooling. The mixture was stirred at room temperature for 1 hr. A half amount of the solvent was evaporated under reduced pressure, and the residue was diluted with ethyl acetate, washed successively with water, 1N aqueous sodium hydroxide solution, water and saturated brine and dried over magnesium sulfate. The solvent was evaporated and the obtained solid was washed with isopropyl ether to give the title compound (117 g) as colorless flakes.

Workup

  1. temperaturecooling
  2. customA half amount of the solvent was evaporated under reduced pressure
  3. additionthe residue was diluted with ethyl acetate
  4. washwashed successively with water, 1N aqueous sodium hydroxide solution, water and saturated brine
  5. dry with materialdried over magnesium sulfate
  6. customThe solvent was evaporated
  7. washthe obtained solid was washed with isopropyl ether

Sources & evidence

ORD record
ord-d7a6da0d23cd412b8dd5363bbc21bb3f
Source dataset
uspto-grants-2005_11
Patent number
US06960586B2

Reaction notes

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