Triethylamine → 2-Acrylethylmethacrylamide

HRID 2415400

Reaction equation

HRID 2415400 reaction equation
OCC[NH:4][C:5](=[O:9])[C:6]([CH3:8])=[CH2:7].C(N([CH2:15][CH3:16])CC)C.[C:17](Cl)(=[O:20])[CH:18]=[CH2:19]>C(Cl)(Cl)Cl>[C:17]([CH2:15][CH2:16][CH:7]=[C:6]([CH3:8])[C:5]([NH2:4])=[O:9])([CH:18]=[CH2:19])=[O:20]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 13140Acryloyl chlorideHCID 10197699N-(2-Hydroxyethyl)methacrylamide

Product 1

HCID 865836782-Acrylethylmethacrylamide

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a stirred solution of N-(2-hydroxyethyl)methacrylamide (10 mmol, 1.3 g) and triethylamine (11 mmol, 1.5 cm3) in chloroform (40 cm3), was added dropwise, a solution of acryloyl chloride (11 mmol, 0.9 cm3) in chloroform (20 cm3) at room temperature under a nitrogen atmosphere. After the addition was complete, the reaction mixture was stirred for a further 16 h. The usual work-up as for example 1 then gave the crosslinking monomer, 2-acrylethylmethacrylamide (Rf 0.54) as a clear, colorless oil (0.6 g, 32%). δH (400 MHz; CDCl3) 6.45 (1H, br m). NH; 6.38 (1H, dd, J 17.8, 2.0 Hz), ROOCH═CHaHb; 6.08 (1H, dd, J 17.8, 8.9 Hz), ROOCH═CHaHb; 5.82 (1H, dd, J 8.9, 2.0 Hz), ROOCH═CHaHb:5.66 (1H, s), RHNOC(H3C)C═CHcHd; 5.29 (1H, s), RHNOC(H3C)C═CHcHd; 4.25 (2H, t, J 4.9 Hz), CH2OCO; 3.57 (2H, td, J 4.9, 4.7 Hz), CHNHCO; 1.94 (3H, s), CH3. δC(75.4 MHZ; CDCl3) 168.52, HNC═O; 166.22, OC═O; 139.60, RHNOC(H3C)C═CH2; 131.34, ROOCH═CH2; 127.83, ROOCH═CH2; 119.69, RHNOC(H3C)C═CH2; 63.07, CH2OC═O; 38.97, CH2NHC═O; 18.43, CH3. Found: M+. 183.22.

Workup

  1. customat room temperature
  2. additionAfter the addition

Sources & evidence

ORD record
ord-3f0aa86361114913aa2b635788aebb63
Source dataset
uspto-grants-2004_11
Patent number
US06818718B2

Linked notes

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