P-Chloroacetophenone → (2E)-1-(4-chlorophenyl)-3-(dimethylamino)prop-2-en-1-one

HRID 976266

Reaction equation

[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][C:7]([Cl:10])=[CH:6][CH:5]=1)=[O:3].C(O[CH:14](OCC)[N:15]([CH3:17])[CH3:16])C>>[CH3:14][N:15]([CH3:17])[CH:16]=[CH:1][C:2]([C:4]1[CH:9]=[CH:8][C:7]([Cl:10])=[CH:6][CH:5]=1)=[O:3]

Participants

Reactant 2

HCID 7467P-Chloroacetophenone

HCID 70913Dimethylformamide diethylacetal

Product 1

HCID 605938(2E)-1-(4-chlorophenyl)-3-(dimethylamino)prop-2-en-1-one

Procedure

Stage 3.05 g (3.23 mmol) of 4-chloroacetophenone are stirred in 3.6 ml of dimethylformamide diethylacetal for 17.5 h at 110°. After cooling, precipitation is effected with hexane and the precipitate is isolated by filtration and dried. 3-dimethylamino-1(4-chloro-phenyl)-2-propen-1-one is obtained; 1H-NMR (DMSO): 2.9 (3H,s), 3.1 (3H,s), 5.8 (1H,d), 7.5 (2H,m), 7.75 (1H,d), 7.95 (2H,m).

Workup

temperatureAfter cooling
customprecipitation
customthe precipitate is isolated by filtration
customdried

Sources & evidence

ORD record: ord-9ff147db5e9a46c7b4655915371f96df
Source dataset: uspto-grants-1997_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05612340

Linked notes

Loading…