Water → Ibrolipim

HRID 53103

反応式

HRID 53103 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>[CH2:24]([O:23][P:21]([CH2:26][C:27]1[CH:28]=[CH:29][C:30]([C:31]([NH:1][C:2]2[CH:9]=[CH:8][C:7]([Br:10])=[CH:6][C:3]=2[C:4]#[N:5])=[O:32])=[CH:34][CH:35]=1)([O:20][CH2:18][CH3:19])=[O:22])[CH3:25]

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 6344Dichloromethane溶媒2 回

実験手順

2-Amino-5-bromobenzonitrile (3.94 g, 20 millimoles), triethylamine (2.22 g, 22 millimoles) and 4-dimethylamino- pyridine (0.49 g, 4 millimoles) were dissolved in 40 ml of dry dichloromethane, to which was slowly added dropwise a solution of 4-diethoxyphosphinoylmethylbenzoyl chloride (5.81 g, 20 millimoles) in 40 ml dry dichloromethane while cooling the system with ice and stirring it. After stirring the resulting mixture at ambient temperature for 10 hours, the reaction mixture was mixed with 50 ml of water and extracted with chloroform. The chloroform layer was dried on anhydrous sodium sulfate and the solvent was removed by evaporation under reduced pressure. Purification of the residue by a silica gel column chromato-graphy using 1:2 mixture of chloroform and ethyl acetate as an eluent, followed by recrystallization from benzene-n-hexane mixture, gave 2.94 g of 4-diethoxyphosphinoylmethyl-N-(4-bromo-2-cyanophenyl)benzamide as a colorless crystalline product melting at 165°-166° C. (after recrystallization from benzene-n-hexane).

後処理

  1. temperaturewhile cooling the system with ice
  2. stirringAfter stirring the resulting mixture at ambient temperature for 10 hours
  3. extractionextracted with chloroform
  4. dry with materialThe chloroform layer was dried on anhydrous sodium sulfate
  5. customthe solvent was removed by evaporation under reduced pressure
  6. customPurification of the residue by a silica gel column chromato-graphy
  7. addition1:2 mixture of chloroform and ethyl acetate as an eluent
  8. customfollowed by recrystallization from benzene-n-hexane mixture

出典と根拠

ORDレコード
ord-e2c226ef8c37439f84128e81a40a5d78
出典データセット
uspto-grants-1997_04
特許番号
US05618801

関連ノート

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