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

HRID 2384316ノート

反応式

HRID 2384316 の反応式
[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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒2 回HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-e20f65288f2848c1928d81c74a7e9963
出典データセット
uspto-grants-2012_09
特許番号
US08263657B2

反応ノート

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