Hydrochloric Acid → cinnamyl-N-methyl-3,4,5-trimethoxyphenylpropiolamide

HRID 1282921ノート

反応式

HRID 1282921 の反応式
[CH3:1][NH:2][C:3](=[O:18])[C:4]#[C:5][C:6]1[CH:11]=[C:10]([O:12][CH3:13])[C:9]([O:14][CH3:15])=[C:8]([O:16][CH3:17])[CH:7]=1.[H-].[Na+].[CH2:21](Br)[CH:22]=[CH:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.Cl>CN(C)C=O.O>[CH2:21]([N:2]([CH3:1])[C:3](=[O:18])[C:4]#[C:5][C:6]1[CH:7]=[C:8]([O:16][CH3:17])[C:9]([O:14][CH3:15])=[C:10]([O:12][CH3:13])[CH:11]=1)[CH:22]=[CH:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 98116BromomethylstyreneHCID 21445696N-methyl-3,4,5-trimethoxyphenylpropiolamide

生成物 1

HCID 54089509cinnamyl-N-methyl-3,4,5-trimethoxyphenylpropiolamide

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒3 回

実験手順

The solution of 10.0 g of N-methyl-3,4,5-trimethoxyphenylpropiolamide in 80 ml of dimethylformamide is added dropwise to the suspension of 1.05 g of sodium hydride in 10 ml of dimethylformamide while stirring and cooling with ice. The mixture is stirred for 1 hour at room temperature whereupon the solution of 8.0 g of cinnamyl bromide in 40 ml of dimethylformamide is added dropwise and stirring is continued for 15 hours at room temperature. The mixture is poured into the solution of 20 ml of 3N hydrochloric acid in 600 ml of water and the whole is extracted with 250 ml of toluene. The extract is washed with 2N aqueous sodium hydroxide and saturated aqueous sodium chloride, dried and filtered, to yield the desired toluene-solution of the N-cinnamyl-N-methyl-3,4,5-trimethoxyphenylpropiolamide.

後処理

  1. temperaturecooling with ice
  2. additionis added dropwise
  3. stirringstirring
  4. extractionthe whole is extracted with 250 ml of toluene
  5. washThe extract is washed with 2N aqueous sodium hydroxide and saturated aqueous sodium chloride
  6. customdried
  7. filtrationfiltered

出典と根拠

ORDレコード
ord-14bb0fa91c264522942f62d1377cb02c
出典データセット
uspto-grants-1976_08
特許番号
US03973030

反応ノート

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