Triethylamine → N-methyl-N-(3-methyl-benzo[b]thiophen-2-ylmethyl)acrylamide

HRID 1362053ノート

反応式

HRID 1362053 の反応式
[CH3:1][NH:2][CH2:3][C:4]1[S:8][C:7]2[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=2[C:5]=1[CH3:13].[C:14](Cl)(=[O:17])[CH:15]=[CH2:16].C(N(CC)CC)C>C(Cl)Cl>[CH3:1][N:2]([CH2:3][C:4]1[S:8][C:7]2[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=2[C:5]=1[CH3:13])[C:14](=[O:17])[CH:15]=[CH2:16]

参加物

5

反応物 3

HCID 8471TriethylamineHCID 13140Acryloyl chlorideHCID 22593745N-methyl(3-methylbenzo[b]thiophen-2-yl)methanamine

生成物 1

HCID 17930139N-methyl-N-(3-methyl-benzo[b]thiophen-2-ylmethyl)acrylamide収率 75.1%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

A solution of methyl-(3-methyl-benzo[b]thiophen-2-ylmethyl)amine (1.95 g, 11.4 mmol) in CH2Cl2 (40 mL) was treated with acryloyl chloride (1.2 mL, 14 mmol) and triethylamine (3.2 mL, 22 mmol). The mixture was stirred at room temperature for 1 h. The reaction mixture was diluted with CH2Cl2 (100 mL). The solution was washed with water and brine, dried over Na2SO4, filtered and concentrated under reduced pressure. Purification by column chromatography (silica gel, EtOAc/hexanes, 40/60) gave the title compound (2.10 g, 75%) as a pale yellow solid: MS (ESI) m/e 246 (M+H)+.

後処理

  1. washThe solution was washed with water and brine
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customPurification by column chromatography (silica gel, EtOAc/hexanes, 40/60)

出典と根拠

ORDレコード
ord-6240a5f7ba0d48be9f35751b0c5878e9
出典データセット
uspto-grants-2011_02
特許番号
US07879872B2

反応ノート

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