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Water → Ibrolipim

HRID 650502
ノート
印刷プレビュー

反応式

HRID 650502 の反応式
[NH2:1][C:2]1[CH:9]=[CH:8][C:7]([Br:10])=[CH:6][C:3]=1[C:4]#[N:5].C(N(CC)CC)C.[CH2:18]([O:20][P:21]([CH2:26][C:27]1[CH:35]=[CH:34][C:30]([C:31](Cl)=[O:32])=[CH:29][CH:28]=1)([O:23][CH2:24][CH3:25])=[O:22])[CH3:19].O>CN(C)C1C=CN=CC=1.ClCCl>[Br:10][C:7]1[CH:8]=[CH:9][C:2]([NH:1][C:31]([C:30]2[CH:34]=[CH:35][C:27]([CH2:26][P:21](=[O:22])([O:20][CH2:18][CH3:19])[O:23][CH2:24][CH3:25])=[CH:28][CH:29]=2)=[O:32])=[C:3]([C:4]#[N:5])[CH:6]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 962WaterHCID 8471TriethylamineHCID 4297402-Amino-5-bromobenzonitrileHCID 104469734-[(Diethoxyphosphoryl)-methyl]benzoyl chloride

生成物 1

HCID 131601Ibrolipim収率 32.6%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒
HCID 6344
Dichloromethane
溶媒
2 回

実験手順

3.94 Grams (20 millimoles) of 2-amino-5-bromo-benzonitrile, 2.22 g (22 millimoles) of triethylamine and 0.49 g (4 millimoles) of 4-dimethylaminopyridine were dissolved in 40 ml of dry dichloromethane, under ice-cooling there was added dropwise slowly 40 ml of dry dichloromethane solution of 5.81 g (20 millimoles) of 4-diethoxyphosphorylmethylbenzoyl chloride with stirring. The reaction was carried out at room temperature for 10 hours, to this reaction mixture was added 50 ml of water, then extracted with chloroform and the organic layer was dried over anhydrous sodium sulfate, next the solvent was removed by distillation under reduced pressure. Thus obtained residue was refined by means of a silica gel column chromatography (eluted with chloroform: ethyl acetate=1:2), recrystallized from benzen-n-hexane, there was obtained 2.94 g of diethyl 4-[N-(4-bromo-2-cyanophenyl)carbamoyl]benzylphosphonate as colorless crystals.

後処理

  1. temperaturecooling there
  2. extractionextracted with chloroform
  3. dry with materialthe organic layer was dried over anhydrous sodium sulfate, next the solvent
  4. customwas removed by distillation under reduced pressure
  5. washThus obtained residue was refined by means of a silica gel column chromatography (eluted with chloroform: ethyl acetate=1:2)
  6. customrecrystallized from benzen-n-hexane

出典と根拠

ORDレコード
ord-3e858a521f0046a8b3e02947674c4abf
出典データセット
uspto-grants-2001_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06274571B1

反応ノート

読み込み中…

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