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Dimethyl Sulfoxide → HCID 22938350、化合物

HRID 856640
ノート
印刷プレビュー

反応式

HRID 856640 の反応式
F[C:2]1[CH:19]=[CH:18][C:5]([C:6]([C:8]2[C:13]([O:14][CH2:15][CH2:16][CH3:17])=[CH:12][CH:11]=[CH:10][N:9]=2)=[O:7])=[CH:4][CH:3]=1.[N-:20]=[N+]=[N-].[Na+].CS(C)=O>O>[NH2:20][C:2]1[CH:19]=[CH:18][C:5]([CH:6]([C:8]2[C:13]([O:14][CH2:15][CH2:16][CH3:17])=[CH:12][CH:11]=[CH:10][N:9]=2)[OH:7])=[CH:4][CH:3]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 679Dimethyl SulfoxideHCID 33557Sodium AzideHCID 229388512-(4-Fluorobenzoyl)-3-propoxypyridine

生成物 1

HCID 22938350HCID 22938350、化合物収率 63.5%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

A solution of 2-(4-fluorobenzoyl)-3-propoxypyridine (4.46 g) and sodium azide (3.34 g) in. DMSO (50 ml) was stirred for 22 hours at 90° C. To the reaction mixture was added water, and the mixture was extracted with diethylether. The organic layer was washed with saturated brine, dried over magnesium sulfate and concentrated under reduced pressure, and a solution of the residue (4.8 g) in THF (50 ml) was added dropwise to a suspension of aluminum lithium hydride (1.3 g) in. THF (40 ml) at 0° C. The mixture was stirred at room temperature for 30 minutes, water (1.3 ml), 15% aqueous solution of sodium hydroxide (1.3 ml) and water (3.9 ml) were sequentially and slowly added dropwise to the solution at 0° C. The mixture was stirred at room temperature for 2 hours, magnesium sulfate was added to the mixture, and the precipitates were removed by filtration (Celite). The reaction mixture was concentrated under reduced pressure, and the residue was recrystallized from ethyl acetate to give (4-aminophenyl)(3-propoxypyridin-2-yl)methanol (2.82 g) as pale yellow crystals.

後処理

  1. extractionthe mixture was extracted with diethylether
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. additiona solution of the residue (4.8 g) in THF (50 ml) was added dropwise to a suspension of aluminum lithium hydride (1.3 g) in
  6. customat 0° C
  7. additionslowly added dropwise to the solution at 0° C
  8. stirringThe mixture was stirred at room temperature for 2 hours
  9. additionmagnesium sulfate was added to the mixture
  10. customthe precipitates were removed by filtration (Celite)
  11. concentrationThe reaction mixture was concentrated under reduced pressure
  12. customthe residue was recrystallized from ethyl acetate

出典と根拠

ORDレコード
ord-e9c7cf1dce374e60a0ccdcb90cccebb1
出典データセット
uspto-grants-2007_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07262185B2

反応ノート

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