Benzoyl chloride → N-(4-chloro-2-hydroxyphenyl)benzamide

HRID 220811

Reaction equation

HRID 220811 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[OH:9].C(=O)(O)[O-].[Na+].[C:15](Cl)(=[O:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>CCOC(C)=O.O>[Cl:8][C:5]1[CH:6]=[CH:7][C:2]([NH:1][C:15](=[O:22])[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[C:3]([OH:9])[CH:4]=1

Participants

6

Reactant 3

HCID 7412Benzoyl chlorideHCID 915912-Amino-5-chlorophenolHCID 516892Sodium Bicarbonate

Product 1

HCID 57555405N-(4-chloro-2-hydroxyphenyl)benzamideYield 82.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-Amino-5-chlorophenol (1.45 g, 10 mmol) was dissolved in EtOAc (30 ml) and water (20 ml). Sodium bicarbonate (1.25 g, 15 mmol) then benzoyl chloride (1.42 g, 10 mmol) were added and the mixture was stirred at room temperature for 1 h. The layers were partitioned and the organic layer was washed with brine, dried and concentrated in vacuo. The residue was triturated with di-ethyl ether to yield the title compound (2.05 g, 82%).

Workup

  1. customThe layers were partitioned
  2. washthe organic layer was washed with brine
  3. customdried
  4. concentrationconcentrated in vacuo
  5. customThe residue was triturated with di-ethyl ether

Sources & evidence

ORD record
ord-10d36463adb94f57853f5b42f12f0bdb
Source dataset
uspto-grants-2012_06
Patent number
US08202858B2

Linked notes

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