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

HRID 1362053Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1362053
[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]

Komponenten

5

Edukt 3

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

Produkt 1

HCID 17930139N-methyl-N-(3-methyl-benzo[b]thiophen-2-ylmethyl)acrylamideAusbeute 75,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

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)+.

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-6240a5f7ba0d48be9f35751b0c5878e9
Quelldatensatz
uspto-grants-2011_02
Patentnummer
US07879872B2

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