Sodium Hydroxide → HCID 66815809, compound

HRID 1697083Notes

Reaction equation

HRID 1697083 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[C:4]([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:3]=1.[CH:18]([C:20]1[CH:25]=[CH:24][C:23]([S:26]([NH:29][CH2:30][C:31]([OH:34])([CH3:33])[CH3:32])(=[O:28])=[O:27])=[CH:22][CH:21]=1)=O.[OH-].[Na+]>CO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH:9]=[CH:18][C:20]2[CH:25]=[CH:24][C:23]([S:26]([NH:29][CH2:30][C:31]([OH:34])([CH3:32])[CH3:33])(=[O:28])=[O:27])=[CH:22][CH:21]=2)=[C:4]([NH:11][C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:3]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 59846167HCID 59846167, compoundHCID 598461761-(4-Chloro-2-phenylaminophenyl)ethanone

Product 1

HCID 66815809HCID 66815809, compoundYield 68.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a mixture of 1-(4-chloro-2-phenylaminophenyl)ethanone (0.401 g) and 4-formyl-N-(2-hydroxy-2-methylpropyl)-benzene sulfonamide (0.420 g) in MeOH (10 mL) was added NaOH (1.35 mL, 2 N, aq), and the mixture stirred overnight at RT. The product was concentrated under reduced pressure, washed with EtOAc, H2O and brine, then dried over Na2SO4. The partially-purified product was chromatographed on anhydrous silica (DCM for 0-10 min, then MeOH/DCM for 11-30 min) to provide 4-[3-(4-chloro-2-phenylaminophenyl)-3-oxo-propenyl]-N-(2-hydroxy-2-methylpropyl)-benzene sulfonamide (0.540 g).

Workup

  1. concentrationThe product was concentrated under reduced pressure
  2. washwashed with EtOAc, H2O and brine
  3. dry with materialdried over Na2SO4
  4. customThe partially-purified product was chromatographed on anhydrous silica (DCM for 0-10 min

Sources & evidence

ORD record
ord-ebf041be4d83404395dd4649febd8378
Source dataset
uspto-grants-2012_04
Patent number
US08163906B2

Reaction notes

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