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Water → N-[2-(3,5-dichloropyridin-2-yl)-2-oxoethyl]phthalimide

HRID 55984
ノート
印刷プレビュー

反応式

HRID 55984 の反応式
Br[CH2:2][C:3]([C:5]1[C:10]([Cl:11])=[CH:9][C:8]([Cl:12])=[CH:7][N:6]=1)=[O:4].[C:13]1(=[O:23])[NH:17][C:16](=[O:18])[C:15]2=[CH:19][CH:20]=[CH:21][CH:22]=[C:14]12.[K].O>CN(C)C=O>[Cl:11][C:10]1[C:5]([C:3](=[O:4])[CH2:2][N:17]2[C:16](=[O:18])[C:15]3=[CH:19][CH:20]=[CH:21][CH:22]=[C:14]3[C:13]2=[O:23])=[N:6][CH:7]=[C:8]([Cl:12])[CH:9]=1
参加物反応条件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 962WaterHCID 24194345Phthalimide potassium saltHCID 534166072-Bromo-1-(3,5-dichloropyridin-2-yl)ethanone

生成物 1

HCID 118071534N-[2-(3,5-dichloropyridin-2-yl)-2-oxoethyl]phthalimide収率 8.6%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

To 3.00 g of the 2-bromo-1-(3,5-dichloropyridin-2-yl)ethanone prepared in Step 2 in Synthetic Example 2 in 30 ml of N,N-dimethylformamide, 4.13 g of potassium phthalimide was added, and the mixture was stirred at 80° C. for 3 hours and then at room temperature for 18 hours. After completion of the reaction, the reaction mixture was mixed with 150 ml of water and extracted with ethyl acetate (50 ml×2), the resulting organic layers were combined, washed with water (50 ml×1) and dried over saturated aqueous sodium chloride and then anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The resulting residue was mixed with 40 ml of a mixture of diisopropyl ether and hexane (1:1), the insolubles were filtered off, and the solvent was evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography using ethyl acetate-hexane (with a gradient of from 15:85 to 25:75) as the eluent to obtain 0.32 g of the desired product as a dark brown resinous substance.

後処理

  1. waitat room temperature for 18 hours
  2. customAfter completion of the reaction
  3. extractionextracted with ethyl acetate (50 ml×2)
  4. washwashed with water (50 ml×1)
  5. dry with materialdried over saturated aqueous sodium chloride
  6. customanhydrous sodium sulfate, and the solvent was evaporated under reduced pressure
  7. additionThe resulting residue was mixed with 40 ml of a mixture of diisopropyl ether and hexane (1:1)
  8. filtrationthe insolubles were filtered off
  9. customthe solvent was evaporated under reduced pressure
  10. customThe resulting residue was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-b82965e1a9e349b69f71fb8e4ffa5f93
出典データセット
uspto-grants-2016_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09434684B2

反応ノート

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