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

HRID 359085ノート

反応式

HRID 359085 の反応式
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

参加物

6

反応物 4

HCID 6228DimethylformamideHCID 78124-ChloroanilineHCID 516892Sodium BicarbonateHCID 53772867Methyl 4-(3-chloropropoxy)-alpha-methylcinnamate

生成物 1

HCID 53937419methyl 4-[3-[N-(4chlorophenyl)amino]propoxy]-alpha-methylcinnamate収率 54.3%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
100 °C

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-f614b82489724963b16de0b6862bc139
出典データセット
uspto-grants-1991_03
特許番号
US04999378

反応ノート

読み込み中…