Triethylamine → N-(2-Isobutoxy-3-methoxybenzyl)-N-methylacrylamide

HRID 1362280Notes

Reaction equation

HRID 1362280 reaction equation
[CH2:1]([O:5][C:6]1[C:14]([O:15][CH3:16])=[CH:13][CH:12]=[CH:11][C:7]=1[CH2:8]CN)[CH:2]([CH3:4])[CH3:3].[C:17](Cl)(=[O:20])[CH:18]=[CH2:19].[CH2:22]([N:24](CC)CC)C>C(Cl)Cl>[CH2:1]([O:5][C:6]1[C:14]([O:15][CH3:16])=[CH:13][CH:12]=[CH:11][C:7]=1[CH2:8][N:24]([CH3:22])[C:17](=[O:20])[CH:18]=[CH2:19])[CH:2]([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 13140Acryloyl chlorideHCID 60905559HCID 60905559, compound

Product 1

HCID 59277527N-(2-Isobutoxy-3-methoxybenzyl)-N-methylacrylamideYield 92.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of (2-isobutoxy-3-methoxybenzyl)methylamine (2.00 g, 8.96 mmol) in CH2Cl2 (80 mL) was added acryloyl chloride (0.85 mL, 9.8 mmol) drop-wise. After stirring for five minutes, triethylamine (1.37 mL, 9.86 mmol) was added. The solution was stirred for 6 hours. The solution was diluted with CH2Cl2 (30 mL) and then washed with H2O (3×100 mL) and brine (2×100 mL), dried (Na2SO4) and concentrated to yield the title compound (2.30 g, 92%) as a light yellow oil and as a mixture of amide rotamers: 1H NMR (500 MHz, DMSO-d6) δ 7.06-6.93 (m, 2H), 6.85-6.62 (m, 1H), 6.57-6.53 (m, 1H), 6.17-6.13 (m, 1H), 5.73-5.63 (m, 1H), 4.64-4.58 (m, 2H), 3.79-3.78 (m, 3H), 3.69-3.66 (m, 2H), 2.95-2.87 (m, 3H), 2.01-1.98 (m, 1H), 0.99-0.97 (m, 6H).

Workup

  1. stirringThe solution was stirred for 6 hours
  2. washwashed with H2O (3×100 mL) and brine (2×100 mL)
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-1020f69fcbfc4466b9f8a1a1b4d0498c
Source dataset
uspto-grants-2011_02
Patent number
US07879872B2

Reaction notes

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