4-Aminophenol → 2-Chloro-N-(4-hydroxyphenyl)benzamide

HRID 459239Notes

Reaction equation

HRID 459239 reaction equation
[CH:1]1[C:6]([NH2:7])=[CH:5][CH:4]=[C:3]([OH:8])[CH:2]=1.C(N(CC)CC)C.[Cl:16][C:17]1[CH:25]=[CH:24][CH:23]=[CH:22][C:18]=1[C:19](Cl)=[O:20]>ClCCl>[Cl:16][C:17]1[CH:25]=[CH:24][CH:23]=[CH:22][C:18]=1[C:19]([NH:7][C:6]1[CH:5]=[CH:4][C:3]([OH:8])=[CH:2][CH:1]=1)=[O:20]

Participants

5

Reactant 3

HCID 4034-AminophenolHCID 8471TriethylamineHCID 691102-Chlorobenzoyl chloride

Product 1

HCID 5875672-Chloro-N-(4-hydroxyphenyl)benzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A suspension of p-aminophenol linked to the Wang's resin from Step A (1 eq) in dichloromethane was treated with triethylamine (2 ml/mmol) and 2-chloro-benzoyl chloride (10 eq). The mixture reaction was stirred for 1 hour and then the resin was filtered, washed with MeOH/CH2Cl2 several times and dried. The resin was then treated with TEA 95% H2O 5% and stirred at room temperature for 30 minutes. Filtered and washed with dichloromethane/methanol and concentrated to dryness to afford the title compound.

Workup

  1. customThe mixture reaction
  2. filtrationthe resin was filtered
  3. washwashed with MeOH/CH2Cl2 several times
  4. customdried
  5. additionThe resin was then treated with TEA 95% H2O 5%
  6. stirringstirred at room temperature for 30 minutes
  7. filtrationFiltered
  8. washwashed with dichloromethane/methanol
  9. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-72b2e6151f2348a3b9a6ef5f076f82d5
Source dataset
uspto-grants-2007_03
Patent number
US07192982B2

Reaction notes

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