Benzamide → HCID 58119309, compound

HRID 2167486Notes

Reaction equation

HRID 2167486 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([C:11]#[N:12])=[CH:7][CH:6]=1)=O.[C:13]([NH2:21])(=[O:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>>[C:14]1([C:13]2[O:20][CH:2]=[C:3]([C:5]3[CH:10]=[CH:9][C:8]([C:11]#[N:12])=[CH:7][CH:6]=3)[N:21]=2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

3

Reactant 2

HCID 2331BenzamideHCID 986544-(Bromoacetyl)benzonitrile

Product 1

HCID 58119309HCID 58119309, compoundYield 66%

Conditions

Temperature
135 °C

Procedure

The mixture of the 2-bromo-1-(4-cyanophenyl)ethanone (4 g, 17.85 mmol) and benzamide (5.41 g, 44.6 mmol) was heated to 135° C. for 3 hours. Then the reaction mixture was cooled, and partitioned between diethyl ether and water. The aqueous layer was extracted with ether twice, and the combined organic layers were washed with 1N NaOH, 1N HCl, water, and brine, dried over MgSO4. After concentration, the solid residue was dissolved in CHCl3. The insoluable solid was filtered through a frits funnel and discarded. The CHCl3 solution was filtered through a pad of silica and evaporate to dryness to give 2.9 g (66% yield) of 4-(2-phenyl-1,3-oxazol-4-yl)benzonitrile. LCMS: m/z 247.1 (M+H)+.

Workup

  1. temperatureThen the reaction mixture was cooled
  2. custompartitioned between diethyl ether and water
  3. extractionThe aqueous layer was extracted with ether twice
  4. washthe combined organic layers were washed with 1N NaOH, 1N HCl, water, and brine
  5. dry with materialdried over MgSO4
  6. concentrationAfter concentration
  7. dissolutionthe solid residue was dissolved in CHCl3
  8. filtrationThe insoluable solid was filtered through a frits funnel
  9. filtrationThe CHCl3 solution was filtered through a pad of silica
  10. customevaporate to dryness

Sources & evidence

ORD record
ord-a2995ce09eb24ec48d5f6eddbba38e62
Source dataset
uspto-grants-2015_06
Patent number
US09045467B2

Reaction notes

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