Triethylamine → cinnamyl-N-methyl-3,4,5-trimethoxyphenylpropiolamide

HRID 597587

反応式

HRID 597587 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:13]#[C:14][C:15]([OH:17])=O)[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10].C(N(CC)CC)C.ClC(OCC)=O.[CH3:31][NH:32][CH2:33][CH:34]=[CH:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1>O1CCCC1.C(OCC)C.C(Cl)Cl>[CH2:33]([N:32]([CH3:31])[C:15](=[O:17])[C:14]#[C:13][C:5]1[CH:6]=[C:7]([O:11][CH3:12])[C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=1)[CH:34]=[CH:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1

参加物

8

反応物 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 189183N-methyl-3-phenylprop-2-en-1-amineHCID 125218533-(3,4,5-Trimethoxyphenyl)prop-2-ynoic acid

生成物 1

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

試薬・触媒・溶媒 3

HCID 3283Diethyl Ether溶媒3 回HCID 6344Dichloromethane溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

To the solution of 11.8 g of 3,4,5-trimethoxyphenylpropiolic acid in 50 ml of tetrahydrofuran, 7.1 g of triethylamine are added while stirring, followed by 50 ml of diethyl ether. The mixture is cooled with ice and to the resulting suspension the solution of 5.4 g of ethyl chloroformate in 25 ml of diethyl ether is added during 5 minutes. The mixture is stirred for 15 minutes at 0°-5°, whereupon the solution of 7.35 g of N-methylcinnamylamine in 35 ml of diethyl ether is added dropwise, followed by 80 ml of methylene chloride. The mixture is stirred for 30 minutes and allowed to warm to room temperature. It is washed with N hydrochloric acid, N aqueous sodium hydroxide and saturated aqueous sodium chloride, dried and evaporated under reduced pressure, to yield the N cinnamyl-N-methyl- 3,4,5-trimethoxyphenylpropiolamide.

後処理

  1. additionis added during 5 minutes
  2. additionis added dropwise
  3. stirringThe mixture is stirred for 30 minutes
  4. washIt is washed with N hydrochloric acid, N aqueous sodium hydroxide and saturated aqueous sodium chloride
  5. customdried
  6. customevaporated under reduced pressure

出典と根拠

ORDレコード
ord-77fbe492bb3a46448b1d12af98489f01
出典データセット
uspto-grants-1977_03
特許番号
US04014899

関連ノート

読み込み中…