Benzoyl chloride → Benzamide

HRID 381460Notes

Reaction equation

HRID 381460 reaction equation
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([N:12](CC)CC)C>C(#N)C>[C:1]([NH2:12])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 7412Benzoyl chlorideHCID 8471Triethylamine

Product 1

HCID 2331Benzamide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To 3,3′-(3-amino-2,6-pyridinediylbistoxy)]bis(benzonitrile) (1.0g, 2.9 mmol) dissolved in acetonitrile (50 mL) was added benzoyl chloride (0.50 g, 3.5 mmol) and triethylamine (0.45 g, 0.60 mmol). After stirring for 3 hours, the reaction was partitioned between ether and water. The organic layer was separated, washed with water, saturated aqueous sodium bicarbonate, and brine, dried (MgSO4), and the solvent was removed in vacuo. Chromatography on silica gel with ethyl acetate/hexane (1/3) as eluent gave N-[2,6-bist3-cyanophenoxy)-pyridin-3-yl]benzamide; NMR (CDCl3) 8.95 (d,1), 8.25 (s,1), 7.9 (d,1), 7.2-7.7 (m,12), 6.8 (d,1) ppm.

Workup

  1. customthe reaction was partitioned between ether and water
  2. customThe organic layer was separated
  3. washwashed with water, saturated aqueous sodium bicarbonate, and brine
  4. dry with materialdried (MgSO4)
  5. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-05f2dff208ab43628f4b34f2d3954643
Source dataset
uspto-grants-2001_10
Patent number
US06306884B1

Reaction notes

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