4-Aminophenol → Benzamide, N-(4-hydroxyphenyl)-

HRID 1685999Notes

Reaction equation

HRID 1685999 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:16](Cl)(=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>CN(C=O)C>[OH:8][C:5]1[CH:6]=[CH:7][C:2]([NH:1][C:16](=[O:23])[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:3][CH:4]=1

Participants

5

Reactant 3

HCID 4034-AminophenolHCID 7412Benzoyl chlorideHCID 8471Triethylamine

Product 1

HCID 459327Benzamide, N-(4-hydroxyphenyl)-Yield 105.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-aminophenol (4.27 g, 39.1 mmol) in DMF (50 ml) at 0° C. under an atmosphere of argon was added triethylamine (7.44 ml, 53.4 mmol, 1.5 eq). The reaction mixture was stirred for 10 minutes before slow addition of benzoyl chloride (5 g, 35.6 mmol, 1 eq) over a period of 5 minutes. The reaction mixture was allowed to warm to room temperature and stirred over 18 hours. The DMF was removed under reduced pressure and the mixture was treated with ethyl acetate/water. Precipitation of a white solid resulted, which was filtered off and dried under reduced pressure. The title compound (8.0 g) was isolated in 96% yield.

Workup

  1. customThe DMF was removed under reduced pressure
  2. additionthe mixture was treated with ethyl acetate/water
  3. customPrecipitation of a white solid
  4. customresulted
  5. filtrationwhich was filtered off
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-9a8233b2eb2245b4865d853bd923a20b
Source dataset
uspto-grants-2012_04
Patent number
US08148531B2

Reaction notes

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