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

HRID 1362324Notes

Reaction equation

HRID 1362324 reaction equation
[CH3:1][O:2][C:3]1[C:4]([O:12][CH2:13][CH2:14][CH3:15])=[C:5]([CH:9]=[CH:10][CH:11]=1)[CH2:6]CN.[C:16](Cl)(=[O:19])[CH:17]=[CH2:18].C[CH2:22][N:23](CC)CC>C(Cl)Cl>[CH3:1][O:2][C:3]1[C:4]([O:12][CH2:13][CH2:14][CH3:15])=[C:5]([CH:9]=[CH:10][CH:11]=1)[CH2:6][N:23]([CH3:22])[C:16](=[O:19])[CH:17]=[CH2:18]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 13140Acryloyl chlorideHCID 20982692(2-Propoxy-3-methoxy-benzyl)methylamine

Product 1

HCID 57742093N-(3-Methoxy-2-propoxybenzyl)-N-methylacrylamideYield 88.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of (3-methoxy-2-propoxybenzyl)methylamine (1.00 g, 4.78 mmol) in CH2Cl2 (40 mL) was treated with acryloyl chloride (0.42 mL, 5.2 mmol) followed by Et3N (0.74 mL, 5.3 mmol). After stirring for 1.5 h, the solution was diluted with CH2Cl2 (50 mL) and washed with saturated aqueous NaHCO3 (50 mL). The aqueous layer was extracted with CH2Cl2 (50 mL). The combined organic layers were dried over Na2SO4, filtered and concentrated to give the title compound (1.11 g, 88%) as a tan oil and as a mixture of amide rotamers: 1H NMR (300 MHz, CDCl3) δ 7.06-6.94 (m, 2H), 6.85-6.70 (m, 1H), 6.65-6.58 (m, 1H), 6.18-6.13 (m, 1H), 5.73-5.63 (m, 1H), 4.64-4.58 (m, 2H), 3.89-3.84 (m, 2H), 3.79-3.78 (m, 3H), 2.99-2.86 (m, 3H), 1.73-1.66 (m, 2H), 0.97 (t, J=7.4 Hz, 3H).

Workup

  1. washwashed with saturated aqueous NaHCO3 (50 mL)
  2. extractionThe aqueous layer was extracted with CH2Cl2 (50 mL)
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-3a1d2796526042ee878b9291a8ccdce2
Source dataset
uspto-grants-2011_02
Patent number
US07879872B2

Reaction notes

Loading…