Dimethylformamide dimethyl acetal → HCID 67199937, compound

HRID 550567Notes

Reaction equation

HRID 550567 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([NH:10][S:11]([CH2:14][CH3:15])(=[O:13])=[O:12])[CH:7]=[CH:8][CH:9]=1)(=[O:3])[CH3:2].CO[CH:18](OC)[N:19]([CH3:21])[CH3:20]>C(OCC)(=O)C.CO>[CH3:18][N:19]([CH3:21])[CH:20]=[CH:2][C:1]([C:4]1[CH:5]=[C:6]([NH:10][S:11]([CH2:14][CH3:15])(=[O:12])=[O:13])[CH:7]=[CH:8][CH:9]=1)=[O:3]

Participants

4

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 902979HCID 902979, compound

Product 1

HCID 67199937HCID 67199937, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 21584119Ethylacetate methanolSolvent

Conditions

Temperature
150 °C

Procedure

2 g (8.8 mmol) of N-(3-acetyl-phenyl)-ethanesulfonamide were dissolved in 15 ml of N,N-dimethylformamide dimethyl acetal and heated at 150° C. for 12 h. The solvent was removed by reduced pressure distillation to yield a crude which was chromatographied (silica gel) using ethyl acetate/methanol as eluent. 1.4 g (yield=56%) of N-[3-[3-(dimethylamino)-1-oxo-2-propenyl]phenyl]-ethanesulfonamide were obtained.

Workup

  1. customThe solvent was removed by reduced pressure distillation
  2. customto yield a crude which

Sources & evidence

ORD record
ord-34926c25fe3c4cc48aeb37c582eebc87
Source dataset
uspto-grants-2011_05
Patent number
US07947688B2

Reaction notes

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