Dimethylformamide dimethyl acetal → N-[3-[3-(dimethylamino)-1-oxo-2-propenyl]phenyl)-N-ethyl-methanesulfonamide

HRID 550560Notes

Reaction equation

HRID 550560 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([N:10]([CH2:15][CH3:16])[S:11]([CH3:14])(=[O:13])=[O:12])[CH:7]=[CH:8][CH:9]=1)(=[O:3])[CH3:2].CO[CH:19](OC)[N:20]([CH3:22])[CH3:21]>C(OCC)(=O)C.CO>[CH3:19][N:20]([CH3:22])[CH:21]=[CH:2][C:1]([C:4]1[CH:5]=[C:6]([N:10]([CH2:15][CH3:16])[S:11]([CH3:14])(=[O:12])=[O:13])[CH:7]=[CH:8][CH:9]=1)=[O:3]

Participants

4

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 67199519n-(3-Acetyl-phenyl)-n-ethyl-methanesulfonamide

Product 1

HCID 67198287N-[3-[3-(dimethylamino)-1-oxo-2-propenyl]phenyl)-N-ethyl-methanesulfonamideYield 88.6%

Reagents, catalysts & solvents 1

HCID 21584119Ethylacetate methanolSolvent

Procedure

1.1 g (4.56 mmol) of N-(3-acetyl-phenyl)-N-ethyl-methanesulfonamide were dissolved in 10 ml of N,N-dimethylformamide dimethylacetal and the resultant solution was refluxed for 18 hours. The excess of volatile reagent was removed by reduced pressure distillation to yield a crude which was chromatographied over silica gel using a gradient of ethyl acetate/methanol as eluent. 1.2 g of N-[3-[3-(dimethylamino)-1-oxo-2-propenyl]phenyl]-N-ethyl-methanesulfonamide as a yellowish-white solid were obtained (yield 88.6%)

Workup

  1. customThe excess of volatile reagent was removed by reduced pressure distillation
  2. customto yield a crude which

Sources & evidence

ORD record
ord-89f2f8a051bd4d93ad4a46c16513ab80
Source dataset
uspto-grants-2011_05
Patent number
US07947688B2

Reaction notes

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