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

HRID 1816002

反応式

HRID 1816002 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 62652Cuprous chloride触媒HCID 6344Dichloromethane溶媒

実験手順

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)+.

後処理

  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

出典と根拠

ORDレコード
ord-ff8a4e4761bb4141a29ac4fcb93da78c
出典データセット
uspto-grants-2005_04
特許番号
US06881736B1

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