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

HRID 1797305Notes

Reaction equation

HRID 1797305 reaction equation
[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

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-8ff4a0b4c27249e5a21eb3fbb0b19c76
Source dataset
uspto-grants-2006_04
Patent number
US07034015B2

Reaction notes

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