Benzoyl chloride → HCID 20271671, compound

HRID 484640Notes

Reaction equation

HRID 484640 reaction equation
[CH:1]12[CH2:8][CH2:7][CH:4]([CH:5]=[CH:6]1)[CH2:3][NH:2]2.[C:9](Cl)(=[O:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>[OH-].[Na+]>[C:9]([N:2]1[CH2:3][CH:4]2[CH2:7][CH2:8][CH:1]1[CH:6]=[CH:5]2)(=[O:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 7412Benzoyl chlorideHCID 1380072-Azabicyclo[2.2.2]oct-5-ene

Product 1

HCID 20271671HCID 20271671, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

To a solution of 2-azabicyclo[2,2,2]-oct-5-ene (M. P. Cava et al, J. Org. Chem., 30, 3772 (1965)) (3.3 g) in aqueous 2.5N sodium hydroxide (50 ml) was added benzoyl chloride (6 ml) and the mixture stirred vigourously for 1 hour. Extraction into ether (2×100 ml), drying (Na2SO4) and concentration afforded the 2-benzoyl-2-azabicyclo[2,2,2]oct-5-ene (D1a) (3.7 g, 55%).

Workup

  1. extractionExtraction into ether (2×100 ml)
  2. customdrying
  3. concentration(Na2SO4) and concentration

Sources & evidence

ORD record
ord-d42a7107afb74958821e8b63a1e53df5
Source dataset
uspto-grants-1985_08
Patent number
US04533498

Reaction notes

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