Water → 4-Phthalimidobutyronitrile

HRID 1829973ノート

反応式

HRID 1829973 の反応式
[C:1]1(=[O:11])[NH:5][C:4](=[O:6])[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12.[K].O>CN(C=O)C>[C:4]([CH2:3][CH2:2][CH2:1][N:5]1[C:1](=[O:11])[C:2]2=[CH:10][CH:9]=[CH:8][CH:7]=[C:3]2[C:4]1=[O:6])#[N:5]

参加物

4

反応物 2

HCID 962WaterHCID 24194345Phthalimide potassium salt

生成物 1

HCID 2609504-Phthalimidobutyronitrile収率 157.3%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
90 °C

実験手順

A mixture of potassium phthalimide (8.48 g, 0.046 mol) and 4-bromopropylcyanide (6.4 g, 0.043 mol) in 50 ml of anhydrous DMF was stirred at 90° C. for 2 h. After dilution with 300 ml of water, the aqueous solution was extracted with chloroform (80 ml×3). The combined chloroform solution was washed with 0.5% NaOH aqueous solution (80 ml) and water (100 ml), and dried over anhydrous Na2SO4. After evaporation of chloroform, an oil was obtained and 300 ml of water was added. The oil was rapidly solidified. The solid formed was collected by filtration, washed with water, and dried under high vacuum. The product was recrystallized from methanol which was diluted with water, to give white crystals (7.75 g, 84%). 1H NMR (CDCl3) δ 7.87 (dd, 2H), 7.75 (dd, 2H), 3.83 (t, 2H), 2.44 (t, 2H), 2.09 (quintet, 2H).

後処理

  1. extractionAfter dilution with 300 ml of water, the aqueous solution was extracted with chloroform (80 ml×3)
  2. washThe combined chloroform solution was washed with 0.5% NaOH aqueous solution (80 ml) and water (100 ml)
  3. dry with materialdried over anhydrous Na2SO4
  4. customAfter evaporation of chloroform
  5. customan oil was obtained
  6. customThe solid formed
  7. filtrationwas collected by filtration
  8. washwashed with water
  9. customdried under high vacuum
  10. customThe product was recrystallized from methanol which
  11. additionwas diluted with water

出典と根拠

ORDレコード
ord-b893080bbd204140b2fbc41d1f005748
出典データセット
uspto-grants-2006_06
特許番号
US07064218B2

反応ノート

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