p-Toluenesulfonic acid → {2-Chloro-4-[(2-{[2-(2-hydroxyethoxy)ethoxy]methyl}phenyl)amino]phenyl}(2-methylphenyl)methanone

HRID 1797303Notes

Reaction equation

HRID 1797303 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][O:19][CH2:20][CH2:21][O:22]C2CCCCO2)[CH:5]=[CH:4][C:3]=1[C:29]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=1[CH3:37])=[O:30].C1(C)C=CC(S(O)(=O)=O)=CC=1.C([O-])(O)=O.[Na+]>CO>[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][O:19][CH2:20][CH2:21][OH:22])[CH:5]=[CH:4][C:3]=1[C:29]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=1[CH3:37])=[O:30]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 516892Sodium BicarbonateHCID 10118970(2-Chloro-4-{[2-({2-[2-(tetrahydro-2H-pyran-2-yloxy)ethoxy]ethoxy}methyl)phenyl]amino}phenyl)(2-methylphenyl)methanone

Product 1

HCID 10203602{2-Chloro-4-[(2-{[2-(2-hydroxyethoxy)ethoxy]methyl}phenyl)amino]phenyl}(2-methylphenyl)methanone

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Compound 149 (5.68 g, 10.8 mmol) was dissolved in MeOH (100 mL) and p-toluenesulfonic acid (3.09 g, 16.3 mmol) was added. The solution was stirred at room temperature for 2 h. Aqueous NaHCO3 (5%, 100 mL) was added and the water phase was extracted with EtOAc (3×50 mL). The combined organic phases were washed with brine (50 mL), dried (MgSO4) and evaporated in vacuo. The crude product was purified by flash chromatography using EtOAc/Petroleum ether 1:1–3:2 as the eluent to afford the title compound as an orange oil.

Workup

  1. extractionthe water phase was extracted with EtOAc (3×50 mL)
  2. washThe combined organic phases were washed with brine (50 mL)
  3. dry with materialdried (MgSO4)
  4. customevaporated in vacuo
  5. customThe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-7a5b4afd97664151bbbb237180954c8c
Source dataset
uspto-grants-2006_04
Patent number
US07034015B2

Reaction notes

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