Ethanone, 1-(3,4-dichlorophenyl)- → 1-(3,4-Dichlorophenyl)-3-(dimethylamino)prop-2-en-1-one

HRID 231530

Reaction equation

HRID 231530 reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][C:7]([Cl:10])=[C:6]([Cl:11])[CH:5]=1)=[O:3].CO[CH:14](OC)[N:15]([CH3:17])[CH3:16]>>[Cl:11][C:6]1[CH:5]=[C:4]([C:2](=[O:3])[CH:1]=[CH:14][N:15]([CH3:17])[CH3:16])[CH:9]=[CH:8][C:7]=1[Cl:10]

Participants

3

Reactant 2

HCID 75841Ethanone, 1-(3,4-dichlorophenyl)-HCID 78373Dimethylformamide dimethyl acetal

Product 1

HCID 28051561-(3,4-Dichlorophenyl)-3-(dimethylamino)prop-2-en-1-one

Procedure

A mixture of 50.0 g of 3,4-dichloroacetophenone and 75 ml of N,N-dimethylformamide dimethyl acetal was heated under reflux for 6 hours, then allowed to cool for 16 hours. The crystalline precipitate was collected by filtration, washed with hexane and dried. The addition of hexane to the above filtrate precipitated some additional product which was collected by filtration. The precipitates were combined, washed with hexane and dried in vacuo to give 55.0 g of 3',4'-dichloro-3-dimethylaminoacrylophenone as bright yellow crystals.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 6 hours
  3. temperatureto cool for 16 hours
  4. filtrationThe crystalline precipitate was collected by filtration
  5. washwashed with hexane
  6. customdried
  7. additionThe addition of hexane to the above filtrate
  8. customprecipitated some additional product which
  9. filtrationwas collected by filtration
  10. washwashed with hexane
  11. customdried in vacuo

Sources & evidence

ORD record
ord-bb1052c824674d639b76eec8fbf3e767
Source dataset
uspto-grants-1989_07
Patent number
US04847256

Linked notes

Loading…