N-Methyl-N-(4-methoxybenzyl)-4-(2-(methoxycarbonyl)ethenyl)phenylsulfonamid → HCID 19957094, compound

HRID 1769131Notes

Reaction equation

HRID 1769131 reaction equation
[CH3:1][N:2]([CH2:18][C:19]1[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=1)[S:3]([C:6]1[CH:11]=[CH:10][C:9]([CH:12]=[CH:13][C:14]([O:16][CH3:17])=[O:15])=[CH:8][CH:7]=1)(=[O:5])=[O:4].[H][H]>C(O)C.[Pd]>[CH3:1][N:2]([CH2:18][C:19]1[CH:20]=[CH:21][C:22]([O:25][CH3:26])=[CH:23][CH:24]=1)[S:3]([C:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH2:13][C:14]([O:16][CH3:17])=[O:15])=[CH:8][CH:7]=1)(=[O:4])=[O:5]

Participants

5

Reactant 2

HCID 54424125N-Methyl-N-(4-methoxybenzyl)-4-(2-(methoxycarbonyl)ethenyl)phenylsulfonamidHCID 178418361HCID 178418361, compound

Product 1

HCID 19957094HCID 19957094, compoundYield 82.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a suspension of the sulfonamide of Example 331 (c) (2.1 g, 4.54 mmol) in ethanol (125 mL) under nitrogen was added 10% Pd/C (0.6 g). The mixture was placed on a Parr hydrogenator at 50 psi of hydrogen for 2 hours, the catalyst was removed by filtration and the solvent was removed in vacuo. The residue was recrystallized from Et2O/MeOH, extracted with CH2Cl2, washed with water, then brine and was dried over MgSO4. The solvent was removed in vacuo to afford 1.41 g (82%) of N-methyl-N-(4-methoxybenzyl)-4-(2-(methoxycarbonyl)ethyl)phenylsulfonamide as a colorless oil.

Workup

  1. customthe catalyst was removed by filtration
  2. customthe solvent was removed in vacuo
  3. customThe residue was recrystallized from Et2O/MeOH
  4. extractionextracted with CH2Cl2
  5. washwashed with water
  6. dry with materialbrine and was dried over MgSO4
  7. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-a626c51d44af4965ae7dd5b3f2021a56
Source dataset
uspto-grants-1995_01
Patent number
US05380721

Reaction notes

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