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

HRID 2097021Notes

Reaction equation

HRID 2097021 reaction equation
[Cl:1][C:2]1[C:3]([O:11][CH2:12][CH2:13][CH3:14])=[C:4]([CH:8]=[CH:9][CH:10]=1)[CH2:5]CN.[C:15](Cl)(=[O:18])[CH:16]=[CH2:17].[CH2:20]([N:22](CC)CC)C>C(Cl)Cl>[Cl:1][C:2]1[C:3]([O:11][CH2:12][CH2:13][CH3:14])=[C:4]([CH:8]=[CH:9][CH:10]=1)[CH2:5][N:22]([CH3:20])[C:15](=[O:18])[CH:16]=[CH2:17]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 13140Acryloyl chlorideHCID 66967022(3-Chloro-2-propoxybenzyl)methylamine

Product 1

HCID 59277565N-(3-Chloro-2-propoxybenzyl)-N-methylacrylamideYield 89%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of (3-chloro-2-propoxybenzyl)methylamine (0.435 g, 2.04 mmol) in CH2Cl2 (18 mL) was added acryloyl chloride (0.18 mL, 2.24 mmol) drop-wise. After stirring for five minutes, triethylamine (0.531 mL, 2.24 mmol) was added. The solution was stirred under N2 for 18 h. The solution was diluted with CH2Cl2 (30 mL) and then washed with H2O (3×50 mL) and brine (2×100 mL), dried over Na2SO4, filtered and concentrated to yield the title compound (0.48 g, 89%) as a light yellow oil and as a mixture of amide rotamers: 1H NMR (500 MHz, CDCl3) δ 7.31-7.26 (m, 1H), 7.10-6.98 (m, 2H), 6.63-6.37 (m, 2H), 5.77-5.73 (m, 1H), 4.76-4.65 (m, 2H), 3.94-3.89 (m, 2H), 3.01 (s, 3H), 1.89-1.82 (m, 2H), 1.11-1.05 (m, 3H).

Workup

  1. stirringThe solution was stirred under N2 for 18 h
  2. washwashed with H2O (3×50 mL) and brine (2×100 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-9e913a0f0348422bbd72757fcde7fbdf
Source dataset
uspto-grants-2013_05
Patent number
US08450307B2

Reaction notes

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