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

HRID 1711833Notes

Reaction equation

HRID 1711833 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

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)+.

Workup

  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)

Sources & evidence

ORD record
ord-bd021b79a20e43c2adce701ee0a31b50
Source dataset
uspto-grants-2010_09
Patent number
US07790709B2

Reaction notes

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