Benzoyl chloride → N-benzoyl 2-chloro-4-hydroxyaniline

HRID 2233234Notes

Reaction equation

HRID 2233234 reaction equation
Cl.[Cl:2][C:3]1[CH:4]=[C:5]([OH:10])[CH:6]=[CH:7][C:8]=1[NH2:9].[C:11](Cl)(=[O:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(=O)([O-])[O-].[K+].[K+].C(=O)([O-])O.[Na+]>O1CCCC1.C(N(CC)CC)C>[C:11]([NH:9][C:8]1[CH:7]=[CH:6][C:5]([OH:10])=[CH:4][C:3]=1[Cl:2])(=[O:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

7

Reactant 4

HCID 7412Benzoyl chlorideHCID 11430Potassium CarbonateHCID 516892Sodium BicarbonateHCID 125981904-Amino-3-chlorophenol hydrochloride

Product 1

HCID 64787725N-benzoyl 2-chloro-4-hydroxyanilineYield 84%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent

Procedure

Triethylamine was added to a suspension of 3-chloro-4-aminophenol hydrochloride (1.80 g, 10.0 mmol) in tetrahydrofuran (200 ml), benzoyl chloride (3.00 ml, 20.0 mmol) was added and the reaction allowed to stir for 18 hours at ambient temperature. The reaction was filtered and the filtrate was evaporated in vacuo. The residue was dissolved in methanol (200 ml), treated with aqueous potassium carbonate solution (0.6 N, 25 ml, 15 mmol) and the mixture stirred for 4 hours at ambient temperature. Addition of saturated aqueous sodium hydrogen carbonate solution (100 ml) caused precipitation of an off-white solid which was collected by suction filtration. Drying in vacuo yielded N-benzoyl 2-chloro-4-hydroxyaniline (2.08 g, 83% yield) as a pale purple solid:

Workup

  1. additionwas added
  2. filtrationThe reaction was filtered
  3. customthe filtrate was evaporated in vacuo
  4. dissolutionThe residue was dissolved in methanol (200 ml)
  5. stirringthe mixture stirred for 4 hours at ambient temperature
  6. customprecipitation of an off-white solid which
  7. filtrationwas collected by suction filtration
  8. customDrying in vacuo

Sources & evidence

ORD record
ord-50cd6c8034f24ed08fa28c8d2cfea1ca
Source dataset
uspto-grants-2010_05
Patent number
US07709479B1

Reaction notes

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