Dimethylformamide dimethyl acetal → HCID 67199958, compound

HRID 550564Notes

Reaction equation

HRID 550564 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([N:10]([CH2:20][CH3:21])[S:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)(=[O:13])=[O:12])[CH:7]=[CH:8][CH:9]=1)(=[O:3])[CH3:2].CO[CH:24](OC)[N:25]([CH3:27])[CH3:26]>C(OCC)(=O)C.CO>[CH3:24][N:25]([CH3:27])[CH:26]=[CH:2][C:1]([C:4]1[CH:5]=[C:6]([N:10]([CH2:20][CH3:21])[S:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)(=[O:13])=[O:12])[CH:7]=[CH:8][CH:9]=1)=[O:3]

Participants

4

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 67197657n-(3-Acetyl-phenyl)-n-ethyl-benzenesulfonamide

Product 1

HCID 67199958HCID 67199958, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 21584119Ethylacetate methanolSolvent

Procedure

1.05 g (3.46 mmol) of N-(3-acetyl-phenyl)-N-ethyl-benzenesulfonamide 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-benzenesulfonamide as a yellowish-white solid were obtained (yield 96%).

Workup

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

Sources & evidence

ORD record
ord-82528eb01cdc430ab0a4aadfb4c74f4b
Source dataset
uspto-grants-2011_05
Patent number
US07947688B2

Reaction notes

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