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

HRID 1362053노트

반응식

HRID 1362053 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

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)+.

후처리

  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)

출처 및 근거

ORD 기록
ord-6240a5f7ba0d48be9f35751b0c5878e9
출처 데이터셋
uspto-grants-2011_02
특허 번호
US07879872B2

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