Ethyl Acetate → N-[2-chloro-5-(3-dimethylamino-acryloyl)-phenyl]-N-methyl-methanesulfonamide

HRID 40712Notes

Reaction equation

HRID 40712 reaction equation
[C:1]([C:4]1[CH:5]=[CH:6][C:7]([Cl:15])=[C:8]([NH:10][S:11]([CH3:14])(=[O:13])=[O:12])[CH:9]=1)(=[O:3])[CH3:2].CO[CH:18](OC)[N:19]([CH3:21])[CH3:20].[C:24](OCC)(=O)C>CN(C)C=O.C(OCC)(=O)C.CC(O)C>[Cl:15][C:7]1[CH:6]=[CH:5][C:4]([C:1](=[O:3])[CH:2]=[CH:18][N:19]([CH3:21])[CH3:20])=[CH:9][C:8]=1[N:10]([CH3:24])[S:11]([CH3:14])(=[O:13])=[O:12]

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 78373Dimethylformamide dimethyl acetalHCID 22220251N-(5-Acetyl-2-chlorophenyl)methanesulfonamide

Product 1

HCID 67279091N-[2-chloro-5-(3-dimethylamino-acryloyl)-phenyl]-N-methyl-methanesulfonamideYield 40%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 22055037Isopropanol ethyl acetateSolvent

Procedure

1.0 g (4.04 mmol) of N-(5-acetyl-2-chloro-phenyl)-methanesulfonamide were dissolved in 10 ml of dry N,N-dimethylformamide and 2.69 ml (2.41 g) (20.19 mmol) of N,N-dimethylformamide dimethylacetal. The resultant solution was refluxed for 2 hours. The solvent and the excess of volatile reagent was removed by reduced pressure distillation to yield an oil which, in the presence of ethyl acetate, gave 1.04 of a crude. It was chromatographied (silica gel) using ethyl acetate/2-propanol as eluent. 0.51 g of N-[2-chloro-5-(3-dimethylamino-acryloyl)-phenyl]-N-methyl-methanesulfonamide as a yellowish-white solid were obtained (yield 40%).

Workup

  1. customThe solvent and the excess of volatile reagent was removed by reduced pressure distillation
  2. customto yield an oil which

Sources & evidence

ORD record
ord-24f9ba11cb494aa594e7744f959ea93a
Source dataset
uspto-grants-2013_09
Patent number
US08530482B2

Reaction notes

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