Benzene → HCID 20303739, compound

Reaction equation

[NH:1](/[C:8](/[CH3:15])=[CH:9]\[C:10]([O:12][CH2:13][CH3:14])=[O:11])[C:2]1[CH:7]=[CH:6]C=CC=1.[C:16]([Cl:20])(=O)[CH:17]=[CH2:18].[OH2:21].[CH:22]1[CH:27]=CC=C[CH:23]=1>>[C:10]([C:9]1[CH2:23][CH2:22][C:27](=[O:21])[N:1]([C:2]2[CH:7]=[CH:6][C:16]([Cl:20])=[CH:17][CH:18]=2)[C:8]=1[CH3:15])([O:12][CH2:13][CH3:14])=[O:11]

Participants

Reactant 4

HCID 241Benzene2×

HCID 962Water

HCID 13140Acryloyl chloride

HCID 5399016HCID 5399016, compound

Product 1

HCID 20303739HCID 20303739, compound

Procedure

Ethyl β-anilinocrotonate (23.9 g) is dissolved in dry benzene (200 ml) and placed in a flask under a nitrogen atmosphere. Acryloyl chloride (10 g) is dissolved in additional dry benzene (200 ml) and drop-added via a sidearm additional funnel over the course of 11/2 hour. The reaction mixture is allowed to stand at about 25° for one hour, and then poured into water and extracted with methylene chloride. Evaporation of the solvent yields crude 5-carbethoxy-N-(4-chlorophenyl)-6-methyl-3,4-dihydropyrid-2-one (23.3 g) having a melting point of 124°-6° (from hexane/ether).