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

HRID 1686000Notes

Reaction equation

HRID 1686000 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 71%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-aminophenol (30.00 g, 275 mmol) in DMF (120 ml) at 0° C. under an atmosphere of nitrogen was added triethylamine (42.5 ml, 302 mmol, 1.2 eq). The reaction mixture was stirred for 10 minutes before dropwise addition of benzoyl chloride (31.9 ml, 275 mmol, 1.0 eq) over a period of 20 minutes. The reaction mixture was allowed to warm to room temperature and stirred for 18 hours. The reaction mixture was poured in ice cold water (800 ml) with vigorous stirring. A precipitate was collected by filtration and washed with water (2×500 ml). The precipitate was slurried in diethyl ether (1.5 L) and vigorously stirred for 30 minutes. The precipitate was collected by filtration and allowed to dry under reduced pressure to afford the title compound as an off-white solid (41.56 g, 71% yield).

Workup

  1. filtrationA precipitate was collected by filtration
  2. washwashed with water (2×500 ml)
  3. stirringvigorously stirred for 30 minutes
  4. filtrationThe precipitate was collected by filtration
  5. customto dry under reduced pressure

Sources & evidence

ORD record
ord-86d4524b768c4c7f9848f1eac663ec75
Source dataset
uspto-grants-2012_04
Patent number
US08148531B2

Reaction notes

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