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

HRID 1797305노트

반응식

HRID 1797305 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-8ff4a0b4c27249e5a21eb3fbb0b19c76
출처 데이터셋
uspto-grants-2006_04
특허 번호
US07034015B2

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