Dimethylformamide → methyl 4-[3-[N-(4chlorophenyl)amino]propoxy]-alpha-methylcinnamate

HRID 359085Notes

Reaction equation

C(=O)([O-])O.[Na+].[Cl:6][C:7]1[CH:13]=[CH:12][C:10]([NH2:11])=[CH:9][CH:8]=1.CN(C=O)C.Cl[CH2:20][CH2:21][CH2:22][O:23][C:24]1[CH:36]=[CH:35][C:27]([CH:28]=[C:29]([CH3:34])[C:30]([O:32][CH3:33])=[O:31])=[CH:26][CH:25]=1>O>[Cl:6][C:7]1[CH:13]=[CH:12][C:10]([NH:11][CH2:20][CH2:21][CH2:22][O:23][C:24]2[CH:36]=[CH:35][C:27]([CH:28]=[C:29]([CH3:34])[C:30]([O:32][CH3:33])=[O:31])=[CH:26][CH:25]=2)=[CH:9][CH:8]=1

Participants

Conditions

Temperature: 100 °C

Procedure

Sodium hydrogen carbonate (3.5 g), 4-chloroaniline (10.45 g) and DMF (50 ml) were added to methyl 4-(3-chloropropoxy)-α-methylcinnamate (11 g), and the mixture was stirred at 100° C. overnight. After the reaction mixture was allowed to cool, water (200 ml) was added thereto, and further the mixture was stirred at room temperature for 30 minutes. The insoluble product was collected by filtration, washed well with water, and was added cold methanol (20ml) thereto, and the mixture was stirred. The resulting crystal was collected by filtration to give methyl 4-[3-[N-(4chlorophenyl)amino]propoxy]-α-methylcinnamate (8 g). mp. 62°-64° C.

Workup

temperatureto cool
stirringfurther the mixture was stirred at room temperature for 30 minutes
filtrationThe insoluble product was collected by filtration
washwashed well with water
additionwas added cold methanol (20ml)
stirringthe mixture was stirred
filtrationThe resulting crystal was collected by filtration

Sources & evidence

ORD record: ord-f614b82489724963b16de0b6862bc139
Source dataset: uspto-grants-1991_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04999378

Reaction notes

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