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

HRID 2384316노트

반응식

HRID 2384316 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 6344Dichloromethane용매2회HCID 8857Ethyl Acetate용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-e20f65288f2848c1928d81c74a7e9963
출처 데이터셋
uspto-grants-2012_09
특허 번호
US08263657B2

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