Phosphorus oxychloride → HCID 178509740、化合物

HRID 452683ノート

反応式

HRID 452683 の反応式
[NH:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]([NH:12][NH2:13])=[O:11])=[CH:9][C:4]=2[N:3]=[N:2]1.[C:14]([C:16]1[CH:17]=[C:18]([CH2:22][CH2:23][C:24](O)=O)[CH:19]=[CH:20][CH:21]=1)#[N:15].P(Cl)(Cl)(Cl)=O.C(=O)([O-])O.[Na+]>O>[NH:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3[O:11][C:24]([CH2:23][CH2:22][C:18]4[CH:17]=[C:16]([CH:21]=[CH:20][CH:19]=4)[C:14]#[N:15])=[N:13][N:12]=3)=[CH:9][C:4]=2[N:3]=[N:2]1

参加物

6

反応物 4

HCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 138542693-Cyanobenzenepropanoic acidHCID 178514416HCID 178514416、化合物

生成物 1

HCID 178509740HCID 178509740、化合物収率 16.4%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
100 °C

実験手順

A mixture of 1H-benzotriazole-5-carbohydrazide (354 mg, 2.00 mmol), 3-(3-cyanophenyl)propionic acid (350 mg, 2.00 mmol) and phosphorus oxychloride (5 mL) was stirred at 100° C. for 4 hr. After cooling, the reaction mixture was poured into water and neutralized with sodium hydrogen carbonate, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate), and recrystallized from methanol/water to give the title compound (104 mg, yield 16%) as colorless crystals.

後処理

  1. temperatureAfter cooling
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (ethyl acetate)
  7. customrecrystallized from methanol/water

出典と根拠

ORDレコード
ord-6cc29173eb2d432fb8b64fa6719b8c8c
出典データセット
uspto-grants-2013_07
特許番号
US08492378B2

反応ノート

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