4'-Cyanoacetophenone → 1-(4-Cyanophenyl)3-dimethylaminopropen-1-one

HRID 1370072

反応式

HRID 1370072 の反応式
[C:1]([C:4]1[CH:11]=[CH:10][C:7]([C:8]#[N:9])=[CH:6][CH:5]=1)(=[O:3])[CH3:2].CO[CH:14](OC)[N:15]([CH3:17])[CH3:16]>>[C:8]([C:7]1[CH:10]=[CH:11][C:4]([C:1](=[O:3])[CH:2]=[CH:14][N:15]([CH3:17])[CH3:16])=[CH:5][CH:6]=1)#[N:9]

参加物

3

反応物 2

HCID 740444'-CyanoacetophenoneHCID 78373Dimethylformamide dimethyl acetal

生成物 1

HCID 28059521-(4-Cyanophenyl)3-dimethylaminopropen-1-one収率 62.3%

実験手順

A mixture of 4-acetylbenzonitrile (51.84 g, 0.357 mol) and N,N-dimethylformamide dimethyl acetal (142 ml, 1.07 mol) was heated to reflux for 1.5 h. The reaction was cooled to room temperature and the resultant crystalline mass collected by filtration and washed with diethyl ether (4×100 ml) to give 1-(4-cyanophenyl)-3-dimethylaminopropen-1-one as an orange solid (44.56 g). An additional crop of this product (11.40 g) could be obtained by partially concentrating the filtrate. δH (d6DMSO) 8.01 (2H, d, J 8.2 Hz), 7.87 (2H, d, J 8.2 Hz), 7.75 (1H, d, J 12.2 Hz), 5.83 (1H, d, J 12.2 Hz), 3.15 (3H, bs), 2.92 (3H, bs). MS (ESI) 201 (MH+, 100%).

後処理

  1. temperaturewas heated
  2. temperatureto reflux for 1.5 h
  3. filtrationthe resultant crystalline mass collected by filtration
  4. washwashed with diethyl ether (4×100 ml)

出典と根拠

ORDレコード
ord-2a128117f5554bf5852dfff36040f838
出典データセット
uspto-grants-2003_06
特許番号
US06579983B1

関連ノート

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