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

HRID 2097021노트

반응식

HRID 2097021 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-9e913a0f0348422bbd72757fcde7fbdf
출처 데이터셋
uspto-grants-2013_05
특허 번호
US08450307B2

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