Triethylamine → N-(3-Chloro-2-propoxybenzyl)-N-methylacrylamide

HRID 1362275ノート

反応式

HRID 1362275 の反応式
[Cl:1][C:2]1[C:3]([O:11][CH2:12][CH2:13][CH3:14])=[C:4]([CH:8]=[CH:9][CH:10]=1)[CH2:5]CN.[C:15](Cl)(=[O:18])[CH:16]=[CH2:17].[CH2:20]([N:22](CC)CC)C>C(Cl)Cl>[Cl:1][C:2]1[C:3]([O:11][CH2:12][CH2:13][CH3:14])=[C:4]([CH:8]=[CH:9][CH:10]=1)[CH2:5][N:22]([CH3:20])[C:15](=[O:18])[CH:16]=[CH2:17]

参加物

5

反応物 3

HCID 8471TriethylamineHCID 13140Acryloyl chlorideHCID 66967022(3-Chloro-2-propoxybenzyl)methylamine

生成物 1

HCID 59277565N-(3-Chloro-2-propoxybenzyl)-N-methylacrylamide収率 89%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

To a solution of (3-chloro-2-propoxybenzyl)methylamine (0.435 g, 2.04 mmol) in CH2Cl2 (18 mL) was added acryloyl chloride (0.18 mL, 2.24 mmol) drop-wise. After stirring for five minutes, triethylamine (0.531 mL, 2.24 mmol) was added. The solution was stirred under N2 for 18 h. The solution was diluted with CH2Cl2 (30 mL) and then washed with H2O (3×50 mL) and brine (2×100 mL), dried over Na2SO4, filtered and concentrated to yield the title compound (0.48 g, 89%) as a light yellow oil and as a mixture of amide rotamers: 1H NMR (500 MHz, CDCl3) δ 7.31-7.26 (m, 1H), 7.10-6.98 (m, 2H), 6.63-6.37 (m, 2H), 5.77-5.73 (m, 1H), 4.76-4.65 (m, 2H), 3.94-3.89 (m, 2H), 3.01 (s, 3H), 1.89-1.82 (m, 2H), 1.11-1.05 (m, 3H).

後処理

  1. stirringThe solution was stirred under N2 for 18 h
  2. washwashed with H2O (3×50 mL) and brine (2×100 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-c48c4db3756444fcbd955a815608bb6f
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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