Triethylamine → HCID 22022533, Verbindung

Temperatur

0 °C

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—).

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%)

ORD-Eintrag

ord-549ae078fee045b386e638516f0f9e0d

Quelldatensatz

uspto-grants-2002_04

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US06369124B1