Dimethylformamide → Benzamide,4-fluoro-N-methoxy-N-methyl-3-(1-methylethoxy)-

HRID 1874304ノート

反応式

HRID 1874304 の反応式
[F:1][C:2]1[CH:13]=[CH:12][C:5]([C:6]([N:8]([O:10][CH3:11])[CH3:9])=[O:7])=[CH:4][C:3]=1[OH:14].[CH:15](I)([CH3:17])[CH3:16].C([O-])([O-])=O.[Cs+].[Cs+].CN(C=O)C>C(Cl)Cl.O>[F:1][C:2]1[CH:13]=[CH:12][C:5]([C:6]([N:8]([O:10][CH3:11])[CH3:9])=[O:7])=[CH:4][C:3]=1[O:14][CH:15]([CH3:17])[CH3:16]

参加物

7

反応物 4

HCID 6228DimethylformamideHCID 6362Isopropyl iodide2 回HCID 10796Cesium carbonateHCID 594590524-fluoro-3-hydroxy-N-methoxy-N-methylbenzamide

生成物 1

HCID 59459043Benzamide,4-fluoro-N-methoxy-N-methyl-3-(1-methylethoxy)-収率 100%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
50 °C

実験手順

A 2 L round bottom flask equipped with a mechanical stirrer, a N2 inlet, a condenser and a temperature controller, was charged 4-fluoro-3-hydroxy-N-methoxy-N-methylbenzamide (99.6 g, 0.5 mol), isopropyl iodide (110.5 g, 0.65 mol) and Cs2CO3 (195.5 g) and DMF (300 mL). The reaction mixture was heated at 50° C. for 3 h. Isopropyl iodide (17.0 g, 0.1 mol) was added and the reaction was heated at 50° C. for 12 h. The reaction mixture was allowed to cool to rt and water (1 L) and CH2Cl2 (500 mL) were added. The reaction mixture was stirred at rt for 0.5 h, and the organic phase was separated. The aqueous layer was extracted with CH2Cl2 (3×500 mL). The combined organic extracts were washed with water (2×1 L), brine (1 L), dried over MgSO4, filtered and concentrated in vacuo at 40° C. for 18 h to give 4-fluoro-3-isopropoxy-N-methoxy-N-methylbenzamide as an off-white solid (120.0 g, 100%).

後処理

  1. customA 2 L round bottom flask equipped with a mechanical stirrer, a N2 inlet, a condenser
  2. temperaturethe reaction was heated at 50° C. for 12 h
  3. temperatureto cool to rt
  4. customthe organic phase was separated
  5. extractionThe aqueous layer was extracted with CH2Cl2 (3×500 mL)
  6. washThe combined organic extracts were washed with water (2×1 L), brine (1 L)
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo at 40° C. for 18 h

出典と根拠

ORDレコード
ord-7c3a906b8a074566995d4da475136ba4
出典データセット
uspto-grants-2012_11
特許番号
US08304403B2

反応ノート

読み込み中…