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

HRID 1816002

반응식

HRID 1816002 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 62652Cuprous chloride촉매HCID 6344Dichloromethane용매

실험 절차

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)+.

후처리

  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

출처 및 근거

ORD 기록
ord-ff8a4e4761bb4141a29ac4fcb93da78c
출처 데이터셋
uspto-grants-2005_04
특허 번호
US06881736B1

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