Acrylonitrile → 3-(5'-bromo-2'-oxospiro[1,3-dioxane-2,3'-indol]-1'(2'H)-yl)propanenitrile

HRID 853867

反応式

HRID 853867 の反応式
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]12[O:16][CH2:15][CH2:14][CH2:13][O:12]1.[OH-].[CH2:18]([N+:25](C)(C)C)[C:19]1C=CC=C[CH:20]=1.C(#N)C=C>CN(C)C=O>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:20][CH2:19][C:18]#[N:25])[C:6](=[O:11])[C:5]12[O:16][CH2:15][CH2:14][CH2:13][O:12]1

参加物

5

反応物 3

HCID 7855AcrylonitrileHCID 66854Benzyltrimethylammonium hydroxideHCID 7115935'-Bromospiro[[1,3]dioxane-2,3'-indolin]-2'-one

生成物 1

HCID 589325423-(5'-bromo-2'-oxospiro[1,3-dioxane-2,3'-indol]-1'(2'H)-yl)propanenitrile収率 711.1%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
52 °C

実験手順

At room temperature, to a solution of 5′-bromospiro[1,3-dioxane-2,3′-indol]-2′(1′H)-one (2.50 g, 8.80 mmol) in N,N dimethylformamide (39 mL) was added benzyltrimethylammonium hydroxide (40% aq. solution, 0.347 mL, 0.88 mmol, 0.1 mole % ) followed by the dropwise addition of acrylonitrile (1.16 mL, 17.6 mmol, 2 eq). The reaction mixture was heated at 52° C. for 2 hr., cooled to room temperature, quenched with H2O (400 mL) and extracted with Et2O (3×). The combined organic extracts were dried and concentrated. The crude product was purified on Biotage KP silica gel eluting with 96/4 CH2Cl2/CH3CN to give the title compound as a yellow solid (2.11 g, 71% ). NMR (300 Mz, DMSO-d6): consistent; MS: (API-ES+) m/z 361 [M+Na].

後処理

  1. temperature, cooled to room temperature
  2. customquenched with H2O (400 mL)
  3. extractionextracted with Et2O (3×)
  4. customThe combined organic extracts were dried
  5. concentrationconcentrated
  6. customThe crude product was purified on Biotage KP silica gel eluting with 96/4 CH2Cl2/CH3CN

出典と根拠

ORDレコード
ord-1fccbf929a37433b91c152163c1cde9a
出典データセット
uspto-grants-2007_08
特許番号
US07256198B2

関連ノート

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