Benzamide → HCID 58119345, compound

HRID 1187440Notes

Reaction equation

HRID 1187440 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([CH3:14])(=[O:13])=[O:12])=[CH:7][CH:6]=1)=O.[C:15]([NH2:23])(=[O:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>>[CH3:14][S:11]([C:8]1[CH:9]=[CH:10][C:5]([C:3]2[N:23]=[C:15]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[O:22][CH:2]=2)=[CH:6][CH:7]=1)(=[O:13])=[O:12]

Participants

3

Reactant 2

HCID 2331BenzamideHCID 7358232-Bromo-4'-(methylsulfonyl)acetophenone

Product 1

HCID 58119345HCID 58119345, compoundYield 30%

Procedure

The mixture of the 2-bromo-1-[4-(methylsulfonyl)phenyl]ethanone (2 g, 7.2 mmol) and benzamide (0.87 g, 7.2 mmol) was heated to 140˜180° C. for 4 hours. When TLC showed that the reaction had completed, the mixture was cooled, and partitioned between EtOAc and water. The aqueous layer was extracted with EtOAc twice, and the combined organic layers were washed with water and brine, dried over MgSO4. After concentration, the residue was purified by column (eluted by PE:EA=10:1) to afford 0.6 g (yield 30%) of 4-[4-(methylsulfonyl)phenyl]-2-phenyl-1,3-oxazole.

Workup

  1. temperaturewas heated to 140˜180° C. for 4 hours
  2. temperaturethe mixture was cooled
  3. custompartitioned between EtOAc and water
  4. extractionThe aqueous layer was extracted with EtOAc twice
  5. washthe combined organic layers were washed with water and brine
  6. dry with materialdried over MgSO4
  7. concentrationAfter concentration
  8. customthe residue was purified by column (eluted by PE:EA=10:1)

Sources & evidence

ORD record
ord-3047ce90c2404a4c8f6b8102265c21dc
Source dataset
uspto-grants-2014_03
Patent number
US08673941B2

Reaction notes

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