Triethylamine → Ibrolipim

HRID 1090067

反応式

HRID 1090067 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.C(N(CC)C1C=CN=CC=1)C.[CH2:29]([O:31][P:32]([CH2:37][C:38]1[CH:46]=[CH:45][C:41]([C:42](Cl)=[O:43])=[CH:40][CH:39]=1)([O:34][CH2:35][CH3:36])=[O:33])[CH3:30]>ClCCl.O>[CH2:35]([O:34][P:32]([CH2:37][C:38]1[CH:39]=[CH:40][C:41]([C:42]([NH:1][C:2]2[CH:9]=[CH:8][C:7]([Br:10])=[CH:6][C:3]=2[C:4]#[N:5])=[O:43])=[CH:45][CH:46]=1)([O:31][CH2:29][CH3:30])=[O:33])[CH3:36]

参加物

7

反応物 4

HCID 8471TriethylamineHCID 4297402-Amino-5-bromobenzonitrileHCID 104469734-[(Diethoxyphosphoryl)-methyl]benzoyl chlorideHCID 117687514-Diethylaminopyridine

生成物 1

HCID 131601Ibrolipim

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒2 回

実験手順

3.94 Grams (20 mM) of 2-amino-5-bromobenzonitrile, 2.22 g (22 mM) of triethylamine and 0.49 g (4 mM) of 4-diethylaminopyridine were dissolved in 40 ml of anhydrous dichloromethane. To this solution was added dropwise 40 ml of anhydrous dichloromethane solution with 5.81 g (20 mM) of 4-diethoxyphosphinoylmethylbenzoyl chloride at 0° C. with stirring. After the stirring was continued for 10 hours at room temperature, 50 ml of water was added to the reaction mixture, and the whole mixture was extracted with chloroform. The chloroform extracts were dried over anhydrous sodium sulfate and concentrated. Thus obtained residue was purified by means of a silica gel column chromatography (eluted with chloroform:ethyl acetate=1:2). The crude crystals were recrystallized from benzene-n-hexane to yield 2.94 g of 4-diethoxyphosphinoylmethyl-N-(4-bromo-2-cyanophenyl)benzamide as colorless crystals.

後処理

  1. extractionthe whole mixture was extracted with chloroform
  2. dry with materialThe chloroform extracts were dried over anhydrous sodium sulfate
  3. concentrationconcentrated
  4. customThus obtained residue was purified by means of a silica gel column chromatography (eluted with chloroform:ethyl acetate=1:2)
  5. customThe crude crystals were recrystallized from benzene-n-hexane

出典と根拠

ORDレコード
ord-43060edbba47469c855c06a69af44138
出典データセット
uspto-grants-1992_01
特許番号
US05081112

関連ノート

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