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

HRID 968193

반응식

HRID 968193 반응식
[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]

참가 물질

3

반응물 2

HCID 166932',4'-DichloroacetophenoneHCID 70913Dimethylformamide diethylacetal

생성물 1

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

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-6dbf03f698434921a432bb448ff0233b
출처 데이터셋
uspto-grants-2005_10
특허 번호
US06958341B2

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