Acryloyl chloride → 1-Acryloyl-3,4-dimethyl-5-phenylimidazolidin-2-one

HRID 1816002

Reaktionsgleichung

Reaktionsgleichung von HRID 1816002
[CH3:1][N:2]1[CH:6]([CH3:7])[CH:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[NH:4][C:3]1=[O:14].CCN(C(C)C)C(C)C.[C:24](Cl)(=[O:27])[CH:25]=[CH2:26]>C(Cl)Cl.Cl[Cu]>[C:24]([N:4]1[CH:5]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:6]([CH3:7])[N:2]([CH3:1])[C:3]1=[O:14])(=[O:27])[CH:25]=[CH2:26]

Komponenten

6

Edukt 3

HCID 13140Acryloyl chlorideHCID 81531DiisopropylethylamineHCID 2305471,5-Dimethyl-4-phenylimidazolidin-2-one

Produkt 1

HCID 228977581-Acryloyl-3,4-dimethyl-5-phenylimidazolidin-2-oneAusbeute 78 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 62652Cuprous chlorideKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of (4 S, 5 R)1,5-dimethyl-4-phenyl-2-imidazolidinone (45.0 g, 237 mmole) and (i-Pr)2NEt (62 mL, 355 mmole) in CH2Cl2 (1200 mL) was added CuCl (50 mg, 0.51 mmole) then acryloyl chloride (29 mL, 355 mmole), and the mixture was heated to reflux. After 2 hr the mixture was cooled to RT, washed with H2O (3×400 mL), dried over MgSO4, and concentrated. The resulting solid was triturated with Et2O (300 mL) and collected by filtration to give the title compound (45.15 g, 78%): 1H NMR (300 MHz, CDCl3) δ 7.72 (dd, J=17.0, 10.5 Hz, 1 H), 7.20-7.38 (m, 3 H), 7.10-7.20 (m, 2 H), 6.40 (dd, J=17.0, 2.1 Hz, 1 H), 5.77 (dd, J=10.4, 2.0 Hz, 1 H), 5.36 (d, J=8.5 Hz, 1 H), 3.85-4.00 (m, 1 H), 2.85 (s, 3 H), 0.82 (d, J=6.6 Hz, 3 H); MS (ES) m/e 245 (M+H)+.

Aufarbeitung

  1. washwashed with H2O (3×400 mL)
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated
  4. customThe resulting solid was triturated with Et2O (300 mL)
  5. filtrationcollected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-ff8a4e4761bb4141a29ac4fcb93da78c
Quelldatensatz
uspto-grants-2005_04
Patentnummer
US06881736B1

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