Toluene → N-[3-(3-Dimethylaminoacryloyl)phenyl]acetamide

HRID 1018878Notes

Reaction equation

HRID 1018878 reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([NH:10][C:11]([CH3:13])=[O:12])[CH:5]=1)=[O:3].CO[CH:16](OC)[N:17]([CH3:19])[CH3:18].C1(C)C=CC=CC=1>CCOC(C)=O>[CH3:16][N:17]([CH3:19])[CH:18]=[CH:1][C:2]([C:4]1[CH:5]=[C:6]([NH:10][C:11](=[O:12])[CH3:13])[CH:7]=[CH:8][CH:9]=1)=[O:3]

Participants

5

Reactant 3

HCID 1140TolueneHCID 78373Dimethylformamide dimethyl acetalHCID 3462023'-Acetamidoacetophenone

Product 1

HCID 53412415N-[3-(3-Dimethylaminoacryloyl)phenyl]acetamideYield 95%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 3-acetamidoacetophenone (3 kg; Lancaster), dimethylformamide dimethylacetal (7 L; Lancaster) and toluene (12 L; Mallinckrodt) is heated at reflux and methanol collected as it is formed. The mixture is heated overnight and a precipitate forms during this time. The reaction may be monitored by TLC analysis (EtOAc: starting material Rf=0.46; product Rf=0.10) to ensure it goes to completion. The reaction mixture is cooled and the solid is collected by filtration. The cake is washed with hexanes (4 L) then dried to give 3.77 kg (95% yield) of a light yellow powder.

Workup

  1. temperatureis heated
  2. temperatureat reflux
  3. custommethanol collected as it
  4. customis formed
  5. temperatureThe mixture is heated overnight
  6. customThe reaction
  7. temperatureThe reaction mixture is cooled
  8. filtrationthe solid is collected by filtration
  9. washThe cake is washed with hexanes (4 L)
  10. customthen dried

Sources & evidence

ORD record
ord-48a1dc3095074abcb50d8b845d4c0c4a
Source dataset
uspto-grants-2002_11
Patent number
US06485746B1

Reaction notes

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