Dimethylformamide dimethyl acetal → HCID 67199434, compound

HRID 550569Notes

Reaction equation

HRID 550569 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([NH:10][S:11]([CH2:14][CH2:15][CH3:16])(=[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:25](OCC)(=O)C.C(OCC)C>CN(C)C=O>[CH3:19][N:20]([CH3:22])[CH:21]=[CH:2][C:1]([C:4]1[CH:5]=[C:6]([N:10]([CH3:25])[S:11]([CH2:14][CH2:15][CH3:16])(=[O:12])=[O:13])[CH:7]=[CH:8][CH:9]=1)=[O:3]

Participants

5

Reactant 3

HCID 78373Dimethylformamide dimethyl acetalHCID 21584169Diethylether ethylacetateHCID 24704709HCID 24704709, compound

Product 1

HCID 67199434HCID 67199434, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
150 °C

Procedure

1 g (4.14 mmol) of N-(3-acetylphenyl)-1-propane-sulfonamide were dissolved in 10 ml of N,N-dimethylformamide. To the resultant solution 2.77 ml (20.74 mmol) of N,N-dimethylformamide dimethyl acetal were added and heated at 150° C. for 2 h. The solvent was removed by reduced pressure distillation to yield an oil, which was treated with a mixture of ethyl acetate-ethyl ether. A small quantity of a solid precipitated which was discarded. The filtrate was evaporated to dryness, dissolved in dichloromethane, and the organic layer was washed with 4×50 ml of water and evaporated to dryness. 1.23 g (yield=96%) of N-[3-[3-(dimethylamino)-1-oxo-2-propenyl]phenyl]-N-methyl-1-propane-sulfonamide were obtained.

Workup

  1. customThe solvent was removed by reduced pressure distillation
  2. customto yield an oil, which
  3. customA small quantity of a solid precipitated which
  4. customThe filtrate was evaporated to dryness
  5. dissolutiondissolved in dichloromethane
  6. washthe organic layer was washed with 4×50 ml of water
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-f3488e3d39ea46668b0252271802a655
Source dataset
uspto-grants-2011_05
Patent number
US07947688B2

Reaction notes

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