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

HRID 1370072

반응식

[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]

참가 물질

반응물 2

HCID 740444'-Cyanoacetophenone

HCID 78373Dimethylformamide dimethyl acetal

생성물 1

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

실험 절차

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%).

후처리

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

출처 및 근거

ORD 기록: ord-2a128117f5554bf5852dfff36040f838
출처 데이터셋: uspto-grants-2003_06
DOI: 10.6084/m9.figshare.5104873.v1
특허 번호: US06579983B1

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