2-Amino-4-chlorophenol → N-(5-Chloro-2-hydroxyphenyl)-3,5-dichlorobenzamide

HRID 421013Notes

Reaction equation

HRID 421013 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[OH:9].C(N(CC)CC)C.[Cl:17][C:18]1[CH:19]=[C:20]([CH:24]=[C:25]([Cl:27])[CH:26]=1)[C:21](Cl)=[O:22]>ClCCl.C(OCC)(=O)C>[Cl:8][C:6]1[CH:5]=[CH:4][C:3]([OH:9])=[C:2]([NH:1][C:21](=[O:22])[C:20]2[CH:19]=[C:18]([Cl:17])[CH:26]=[C:25]([Cl:27])[CH:24]=2)[CH:7]=1

Participants

6

Reactant 3

HCID 72652-Amino-4-chlorophenolHCID 8471TriethylamineHCID 761913,5-Dichlorobenzoyl chloride

Product 1

HCID 17860185N-(5-Chloro-2-hydroxyphenyl)-3,5-dichlorobenzamideYield 32.4%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

2-Amino-4-chlorophenol (316 mg, 2.2 mmol) and triethylamine (243 mg, 2.4 mmol) were dissolved in dichloromethane (5 mL). A solution of 3,5-dichlorobenzoyl chloride (419 mg, 2 mmol) in dichloromethane (2 mL) was added dropwise under ice cooling and argon atmosphere, and the mixture was stirred at room temperature for 15 hours. After the reaction mixture was diluted with ethyl acetate, washed with water and brine one after another, dried over anhydrous magnesium sulfate, the solvent was evaporated under reduced pressure. The obtained residue was purified by column chromatography on silica gel (n-hexane-ethyl acetate=3:1) to give a light brown solid. The solid was suspended and washed with n-hexane-ethyl acetate under heating at reflux to give the title compound (205 mg, 32.4%) as a white crystal.

Workup

  1. washwashed with water and brine one after another,
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customthe solvent was evaporated under reduced pressure
  4. customThe obtained residue was purified by column chromatography on silica gel (n-hexane-ethyl acetate=3:1)
  5. customto give a light brown solid
  6. washwashed with n-hexane-ethyl acetate
  7. temperatureunder heating
  8. temperatureat reflux

Sources & evidence

ORD record
ord-06a72b8dc54d40c29f944b16309e5c38
Source dataset
uspto-grants-2012_01
Patent number
US08097759B2

Reaction notes

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