o-Toluenesulfonyl chloride → HCID 22099729, compound

HRID 1457647Notes

Reaction equation

HRID 1457647 reaction equation
[CH2:1]([O:3][C:4](=[O:19])[CH2:5][CH2:6][CH2:7][NH:8][C:9]1[CH:18]=[CH:17][CH:16]=[CH:15][C:10]=1[C:11]([O:13][CH3:14])=[O:12])[CH3:2].[CH3:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[S:27](Cl)(=[O:29])=[O:28]>N1C=CC=CC=1>[CH2:1]([O:3][C:4](=[O:19])[CH2:5][CH2:6][CH2:7][N:8]([C:9]1[CH:18]=[CH:17][CH:16]=[CH:15][C:10]=1[C:11]([O:13][CH3:14])=[O:12])[S:27]([C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=1[CH3:20])(=[O:29])=[O:28])[CH3:2]

Participants

4

Reactant 2

HCID 8623o-Toluenesulfonyl chlorideHCID 266836methyl 2-[(4-ethoxy-4-oxobutyl)amino]benzoate

Product 1

HCID 22099729HCID 22099729, compoundYield 90.7%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 2.65 g of methyl 2-[(4-ethoxy-4-oxobutyl)amino]benzoate, 2.0 g of 2-methylphenylsulfonyl chloride and pyridine is heated on a steam bath for 16 hours. The mixture is concentrated under a vacuum (remove pyridine) and 1N HCl added. The mixture is extracted with dichloromethane and the extract washed with 1NHCl, H2O, 1M NaHCO3, brine and dried (Na2SO4). The solution is filtered through a thin pad of hydrons magnesium silicate and the filtrate evaporated to give 3.8 g of solid which is crystallized from ethanol to give crystals, m.p. 100°-102° C.

Workup

  1. temperatureis heated on a steam bath for 16 hours
  2. concentrationThe mixture is concentrated under a vacuum (remove pyridine) and 1N HCl
  3. additionadded
  4. extractionThe mixture is extracted with dichloromethane
  5. washthe extract washed with 1NHCl, H2O, 1M NaHCO3, brine
  6. dry with materialdried (Na2SO4)
  7. filtrationThe solution is filtered through a thin pad of hydrons magnesium silicate
  8. customthe filtrate evaporated

Sources & evidence

ORD record
ord-8fef0a5ed1474e2fb06b85677cec9daf
Source dataset
uspto-grants-1998_12
Patent number
US05849735

Reaction notes

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