N,N-Dimethylglycine → HCID 57701126、化合物

HRID 332578

反応式

HRID 332578 の反応式
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[CH:5]=[O:6].I[C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][CH:20]=1)[C:16]#[N:17].C(=O)([O-])[O-].[Cs+].[Cs+].CN(C)CC(O)=O>[Cu]I.O1CCOCC1>[CH:5]([C:4]1[CH:7]=[CH:8][C:9]([O:10][CH3:11])=[C:2]([CH:3]=1)[O:1][C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][CH:20]=1)[C:16]#[N:17])=[O:6]

参加物

7

反応物 4

HCID 673N,N-DimethylglycineHCID 10796Cesium carbonateHCID 12127IsovanillinHCID 1443413-Iodobenzonitrile

生成物 1

HCID 57701126HCID 57701126、化合物収率 43.7%

試薬・触媒・溶媒 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 312751,4-Dioxane溶媒

反応条件

温度
100 °C

実験手順

In a 350 mL pressure vessel equipped with a stir bar was placed 3-hydroxy-4-methoxy-benzaldehyde (15) (1.5 g, 9.86 mmol), 3-iodo-benzonitrile (3.39 g, 14.8 mmol), cesium carbonate (3.21 g, 9.86 mmol), N,N-dimethylglycine (275 mg, 1.97 mmol), copper(I) iodide (188 mg, 0.986 mmol) and 1,4-dioxane (55 mL). The mixture was heated to 100° C. for 46 hours. The reaction was cooled to room temperature, quenched with water (300 mL) and then extracted with ethyl acetate (3×200 mL). The organic portions were combined, washed with brine (300 mL), dried (MgSO4) and concentrated. The crude material was purified by silica gel column chromatography utilizing 35%, 50%, 75% ethyl acetate/hexanes to produce 1.09 g (42% yield) of (16) as a white solid.

後処理

  1. customIn a 350 mL pressure vessel equipped with a stir bar
  2. temperatureThe reaction was cooled to room temperature
  3. customquenched with water (300 mL)
  4. extractionextracted with ethyl acetate (3×200 mL)
  5. washwashed with brine (300 mL)
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated
  8. customThe crude material was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-7a2fe04db1af45a7a321260c6f33f946
出典データセット
uspto-grants-2014_11
特許番号
US08877816B2

関連ノート

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