Triethylamine → 2-Acryloyl Ethylmaleimide

HRID 1636469Notes

Reaction equation

HRID 1636469 reaction equation
O[CH2:2][CH2:3][C:4]1[C:5]([NH:7][C:8](=[O:10])[CH:9]=1)=[O:6].CCN(CC)CC.[C:18](Cl)(=[O:21])[CH:19]=[CH2:20]>C(Cl)Cl>[C:18]([CH2:2][CH2:3][C:4]1[C:5]([NH:7][C:8](=[O:10])[CH:9]=1)=[O:6])(=[O:21])[CH:19]=[CH2:20]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 13140Acryloyl chlorideHCID 22337974Hydroxy ethylmaleimide

Product 1

HCID 220225332-Acryloyl Ethylmaleimide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

2-Hydroxyethyl maleimide (5 g, 35.4 mmol) and Et3N (4.25 g, 43.0 mmol) was dissolved in 75 mL of methylene chloride and cooled to 0° C. Acryloyl chloride (3.20 g, 35.4 mmol) in 25 mL of methylene chloride was added dropwise over 30 minutes. The solution was stirred at room temperature for 30 minutes followed by refluxing for 1 hour. The triethylamine hydrochloride was removed by filtration and the yellow solution was concentrated. The yellow crystals were purified by sublimation yielding white crystals, m.p. 77-78° C. (5.00 g, 72.3%). 1H-NMR (CDCl3, δ, ppm): 3.81-3.87 (2H, --NCH2 --, t) 4.22-4.33 (2H, --OCH2 --, t), 5.81-5.85 (2H, CH2 =CH, cis), 6.00-6.13 (1H, CH2 =CH--, q), 6.34-6.42 (1H CH2 =CH, trans), 6.73 (2H, --OC--CH=CH--CO--, s). 13C-NMR (CDCl3, δ, ppm): 170.4 (2C, C=O, maleimide), 165.8 (1C, C=O, ester), 134.2 (2C, --CH=CH--), 131.45 (1C, --CH=), 127.9 (1C, CH2 =), 61.5 (1C, β--CH2 --), 36.8 (1C, α--CH2 --).

Workup

  1. temperatureby refluxing for 1 hour
  2. customThe triethylamine hydrochloride was removed by filtration
  3. concentrationthe yellow solution was concentrated
  4. customThe yellow crystals were purified by sublimation
  5. customyielding white crystals, m.p. 77-78° C. (5.00 g, 72.3%)

Sources & evidence

ORD record
ord-af9f38721df24492ad05f9702c5b4333
Source dataset
uspto-grants-2000_03
Patent number
US06034150

Reaction notes

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