N,N-Dimethylglycine → 4-(Methylsulfonylamino)benzaldehyde

HRID 591703Notes

Reaction equation

HRID 591703 reaction equation
Br[C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[CH3:10][S:11]([NH2:14])(=[O:13])=[O:12].CN(C)CC(O)=O.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>CN(C=O)C.CCOC(C)=O.[Cu](I)I>[CH:6]([C:5]1[CH:8]=[CH:9][C:2]([NH:14][S:11]([CH3:10])(=[O:13])=[O:12])=[CH:3][CH:4]=1)=[O:7]

Participants

8

Reactant 4

HCID 673N,N-DimethylglycineHCID 62657Potassium Phosphate, TribasicHCID 707414-BromobenzaldehydeHCID 72879Methanesulfonamide

Product 1

HCID 189253554-(Methylsulfonylamino)benzaldehydeYield 58%

Reagents, catalysts & solvents 3

HCID 83717Copper iodideCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4-bromobenzaldehyde (0.250 g, 1.40 mmol), methanesulfonamide (0.154 g, 1.62 mmol), copper iodide (0.0510 g, 0.270 mmol), N,N-dimethylglycine (0.0280 g, 0.270 mmol), and potassium phosphate tribasic (0.716 g, 3.38 mmol) in DMF (5.00 mL) was stirred at reflux for 16 hours. The mixture was diluted with EtOAc (50 mL), washed with water (50 mL), and then saturated aqueous LiCl (5 mL). The combined aqueous layers were then back-extracted with EtOAc (50 mL). The organic layers were combined, washed with brine (50 mL), dried over Na2SO4, filtered, and the solvent was removed under reduced pressure, to provide N-(4-formylphenyl)methanesulfonamide (0.161 g, 58%) as a yellow oil.

Workup

  1. temperatureat reflux for 16 hours
  2. washwashed with water (50 mL)
  3. extractionThe combined aqueous layers were then back-extracted with EtOAc (50 mL)
  4. washwashed with brine (50 mL)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-744962b5dfe84183ae05aa2731c360d0
Source dataset
uspto-grants-2016_01
Patent number
US09238640B2

Reaction notes

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