Triethylamine → HCID 22022533, 화합물

HRID 23967

반응식

HRID 23967 반응식
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]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 13140Acryloyl chlorideHCID 22337974Hydroxy ethylmaleimide

생성물 1

HCID 22022533HCID 22022533, 화합물

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

반응 조건

온도
0 °C

실험 절차

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—).

후처리

  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%)

출처 및 근거

ORD 기록
ord-5475d76a44554bccaa1c674a0d5b8ca2
출처 데이터셋
uspto-grants-2005_02
특허 번호
US06855745B2

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