Dimethylformamide dimethyl acetal → HCID 67278716, compound

HRID 40710Notes

Reaction equation

HRID 40710 reaction equation
[C:1]([C:4]1[CH:5]=[CH:6][C:7]([F:16])=[C:8]([N:10]([CH3:15])[S:11]([CH3:14])(=[O:13])=[O:12])[CH:9]=1)(=[O:3])[CH3:2].CO[CH:19](OC)[N:20]([CH3:22])[CH3:21]>CCCCCC>[CH3:19][N:20]([CH3:22])[CH:21]=[CH:2][C:1]([C:4]1[CH:5]=[CH:6][C:7]([F:16])=[C:8]([N:10]([CH3:15])[S:11]([CH3:14])(=[O:13])=[O:12])[CH:9]=1)=[O:3]

Participants

4

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 23160555HCID 23160555, compound

Product 1

HCID 67278716HCID 67278716, compoundYield 67.4%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

1.66 g (6.77 mmol) of N-(5-acetyl-2-fluoro-phenyl)-N-methyl-methanesulfonamide were dissolved in 3.35 ml (3.0 g) (25.18 mmol) of N,N-dimethylformamide dimethylacetal and the resultant solution was refluxed for 2.5 hours. The mixture was cooled at room temperature. To the solid formed was added 20 ml of n-hexane and filtered to yield a solid which was crystallized from ethyl acetate. 1.37 g of N-[5-(3-dimethylamino-acryloyl)-2-fluoro-phenyl]-N-methyl-methanesulfonamide as a yellowish-white solid were obtained (yield 67.4%).

Workup

  1. customTo the solid formed
  2. filtrationfiltered
  3. customto yield a solid which
  4. customwas crystallized from ethyl acetate

Sources & evidence

ORD record
ord-c572cadf2ce14664b9baff49140bcccf
Source dataset
uspto-grants-2013_09
Patent number
US08530482B2

Reaction notes

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