2',4'-Dichloroacetophenone → 1-(2,4-Dichlorophenyl)-3-(dimethylamino)prop-2-en-1-one

HRID 968193

Reaction equation

HRID 968193 reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][C:7]([Cl:10])=[CH:6][C:5]=1[Cl:11])=[O:3].C(O[CH:15](OCC)[N:16]([CH3:18])[CH3:17])C>>[Cl:11][C:5]1[CH:6]=[C:7]([Cl:10])[CH:8]=[CH:9][C:4]=1[C:2]([CH:1]=[CH:15][N:16]([CH3:18])[CH3:17])=[O:3]

Participants

3

Reactant 2

HCID 166932',4'-DichloroacetophenoneHCID 70913Dimethylformamide diethylacetal

Product 1

HCID 7300441-(2,4-Dichlorophenyl)-3-(dimethylamino)prop-2-en-1-one

Procedure

Part D. A mixture of 2,4-dichloroacetophenone (10.0 g, 52.9 mmol) and dimethylformamide diethyl acetal (10.0 mL, 58.3 mmol) was heated to reflux for 12 hours, then cooled and evaporated under high vacuum. The residual oil was separated by column chromatography (silica gel, 1:1 ethyl acetate-hexane) to afford the product, 1-(2,4-dichlorobenzoyl)-2-(N,N-dimethylamino)ethene, as a viscous oil (12.11 g, 49.6 mmol, 94%). TLC RF 0.05 (20:80 ethyl acetate-hexane). Spectral data: 1H NMR (300 MHz, CDCl3): δ 7.40 (1H, d, J=2.2 Hz), 7.38-7.23 (3H, m), 5.33 (1H, d, J=12.4 Hz), 3.11 (3H, br s), 2.89 (3H, br s). MS (NH3—CI): m/e 249 (1), 248 (10), 247 (8), 246 (64), 245 (16), 244 (100).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 12 hours
  3. temperaturecooled
  4. customevaporated under high vacuum
  5. customThe residual oil was separated by column chromatography (silica gel, 1:1 ethyl acetate-hexane)

Sources & evidence

ORD record
ord-6dbf03f698434921a432bb448ff0233b
Source dataset
uspto-grants-2005_10
Patent number
US06958341B2

Linked notes

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