4-Toluenesulfonyl chloride → 2-{[2-({3-Chloro-4-[(2-methylphenyl)carbonyl]phenyl}amino)benzyl]oxy}ethyl 4-methylbenzenesulfonate

HRID 1797305ノート

反応式

HRID 1797305 の反応式
[Cl:1][C:2]1[CH:7]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[CH2:15][O:16][CH2:17][CH2:18][OH:19])[CH:5]=[CH:4][C:3]=1[C:20]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[CH3:28])=[O:21].[C:29]1([CH3:39])[CH:34]=[CH:33][C:32]([S:35](Cl)(=[O:37])=[O:36])=[CH:31][CH:30]=1>N1C=CC=CC=1>[CH3:39][C:29]1[CH:34]=[CH:33][C:32]([S:35]([O:19][CH2:18][CH2:17][O:16][CH2:15][C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[NH:8][C:6]2[CH:5]=[CH:4][C:3]([C:20]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[CH3:28])=[O:21])=[C:2]([Cl:1])[CH:7]=2)(=[O:37])=[O:36])=[CH:31][CH:30]=1

参加物

4

反応物 2

HCID 73974-Toluenesulfonyl chlorideHCID 10294143[2-Chloro-4-({2-[(hydroxyethoxy)methyl]phenyl}amino)phenyl](2-methylphenyl)methanone

生成物 1

HCID 103027672-{[2-({3-Chloro-4-[(2-methylphenyl)carbonyl]phenyl}amino)benzyl]oxy}ethyl 4-methylbenzenesulfonate

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

Compound 156 (1.0 g, 2.55 mmol) was dissolved in pyridine (1.3 mL) under an argon atmosphere. The solution was cooled on an ice bath and p-toluenesulfonyl chloride (0.56 g, 2.9 mmol) was added. The suspension was stirred for 3 h at room temperature. The reaction was quenched with water and the water phase was extracted twice with EtOAc. The combined organic phases were washed with brine, dried (Na2SO4), filtered and evaporated in vacuo. The crude product was purified by flash chromatography eluting with EtOAc/petroleum ether 1:2. This afforded the title compound as a yellow oil.

後処理

  1. temperatureThe solution was cooled on an ice bath
  2. customThe reaction was quenched with water
  3. extractionthe water phase was extracted twice with EtOAc
  4. washThe combined organic phases were washed with brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. customevaporated in vacuo
  8. customThe crude product was purified by flash chromatography
  9. washeluting with EtOAc/petroleum ether 1:2

出典と根拠

ORDレコード
ord-8ff4a0b4c27249e5a21eb3fbb0b19c76
出典データセット
uspto-grants-2006_04
特許番号
US07034015B2

反応ノート

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