Benzamide → 4-(4-nitrophenyl)-2-phenyloxazole

HRID 1951590Notes

Reaction equation

HRID 1951590 reaction equation
[C:1]([NH2:9])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[CH2:11][C:12]([C:14]1[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=1)=O>CN1C(=O)CCC1>[N+:20]([C:17]1[CH:18]=[CH:19][C:14]([C:12]2[N:9]=[C:1]([C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[O:8][CH:11]=2)=[CH:15][CH:16]=1)([O-:22])=[O:21]

Participants

4

Reactant 2

HCID 2331BenzamideHCID 668402-Bromo-4'-nitroacetophenone

Product 1

HCID 100614284-(4-nitrophenyl)-2-phenyloxazole

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent2×

Conditions

Temperature
135 °C

Procedure

a mixture of benzamide (3.7 g, 31 mmol), 2-bromo-1-(4-nitrophenyl)ethanone (5.00 g, 20 mmol) and 2.5 mL NMP heated in a 135° C. oil bath. After 30 minutes a precipitate developed. Another 2 mL of NMP was added to dissolve the precipitate. The reaction was heated for a total of 2 hours then removed from the oil bath. The reaction mixture solidified upon cooling. 30-40 mL acetonitrile was added to the solid and the resulting mixture was heated to 90° C. The resulting solution was removed from the oil bath and a precipitate developed upon cooling. The precipitate was collected by filtration (3.4 g, 62%).

Workup

  1. dissolutionto dissolve the precipitate
  2. temperatureThe reaction was heated for a total of 2 hours
  3. customthen removed from the oil bath
  4. temperatureupon cooling
  5. addition30-40 mL acetonitrile was added to the solid
  6. temperaturethe resulting mixture was heated to 90° C
  7. customThe resulting solution was removed from the oil bath
  8. temperatureupon cooling
  9. filtrationThe precipitate was collected by filtration (3.4 g, 62%)

Sources & evidence

ORD record
ord-a52444bd6932481db0cf18ad99a47378
Source dataset
uspto-grants-2013_03
Patent number
US08404722B2

Reaction notes

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