Benzamide → 4-Nitrobenzanilide

HRID 1729119Notes

Reaction equation

HRID 1729119 reaction equation
C(N)(=O)[C:2]1[CH:7]=[CH:6]C=[CH:4][CH:3]=1.[OH2:10].O.[OH-].[CH3:13][N+:14]([CH3:17])(C)C.[N+:18]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)([O-:20])=[O:19]>>[N+:18]([C:21]1[CH:26]=[CH:25][C:24]([C:13]([NH:14][C:17]2[CH:6]=[CH:7][CH:2]=[CH:3][CH:4]=2)=[O:10])=[CH:23][CH:22]=1)([O-:20])=[O:19]

Participants

4

Reactant 3

HCID 2331BenzamideHCID 7416NitrobenzeneHCID 22116808Tetramethylammonium hydroxide dihydrate

Product 1

HCID 770034-NitrobenzanilideYield 90%

Procedure

A three-necked round-bottom flask equipped with a Dean-Strak trap and gas inlet line was charged with benzamide (0.2 mole), tetramethylammonium hydroxide dihydrate (0.2 mole) and nitrobenzene (100 mL). The reaction wasstirred for 8 hours at 65° C. with a continuous stream of air sweeping the surface of the reaction. Approximately 5 mL of water and 40 mL of nitrobenzene was collected in the Dean-Stark trap. Another 100 mL ofnitrobenzene was added and the reaction was allowed to stir overnight. A total of 70 mL of nitrobenzene was collected over this time period. The solution was cooled and water was added which caused the immediate precipitation of 4-nitrobenzanilide, i.e., N-(4-nitrophenyl)benzamide. Thesolution was filtered and a dark brown solid was obtained. The solid was washed with hot hexane and air dried to obtain 43.5 g of 4-nitrobenzanilide (90% yield).

Workup

  1. customA three-necked round-bottom flask equipped with a Dean-Strak trap and gas inlet line
  2. customthe surface of the reaction
  3. customApproximately 5 mL of water and 40 mL of nitrobenzene was collected in the Dean-Stark trap
  4. additionAnother 100 mL ofnitrobenzene was added
  5. customA total of 70 mL of nitrobenzene was collected over this time period
  6. temperatureThe solution was cooled
  7. additionwater was added which
  8. customthe immediate precipitation of 4-nitrobenzanilide, i.e., N-(4-nitrophenyl)benzamide
  9. filtrationThesolution was filtered
  10. customa dark brown solid was obtained
  11. washThe solid was washed with hot hexane and air
  12. customdried

Sources & evidence

ORD record
ord-7c1ff62628064dee8bfb424342e7ddda
Source dataset
uspto-grants-1994_07
Patent number
US05331099

Reaction notes

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