Triethylamine → HCID 22022533, compound

HRID 23967

Reaction equation

HRID 23967 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 22022533HCID 22022533, compound

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-5475d76a44554bccaa1c674a0d5b8ca2
Source dataset
uspto-grants-2005_02
Patent number
US06855745B2

Linked notes

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