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Boron tribromide → 4-{N-[(6-hydroxy-benzothien-3-yl)methyl]-N-[1H-imidazol-1-yl-]amino}benzonitrile

HRID 446168
ノート
印刷プレビュー

反応式

HRID 446168 の反応式
[N:1]1([N:6]([C:19]2[CH:26]=[CH:25][C:22]([C:23]#[N:24])=[CH:21][CH:20]=2)[CH2:7][C:8]2[C:12]3[CH:13]=[CH:14][C:15]([O:17]C)=[CH:16][C:11]=3[S:10][CH:9]=2)[CH:5]=[CH:4][N:3]=[CH:2]1.B(Br)(Br)Br.C([O-])(O)=O.[Na+]>C(Cl)Cl>[OH:17][C:15]1[CH:14]=[CH:13][C:12]2[C:8]([CH2:7][N:6]([C:19]3[CH:26]=[CH:25][C:22]([C:23]#[N:24])=[CH:21][CH:20]=3)[N:1]3[CH:5]=[CH:4][N:3]=[CH:2]3)=[CH:9][S:10][C:11]=2[CH:16]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 694453164-{N-[1H-imidazol-1-yl]-N-[(6-methoxy-benzothien-3-yl)methyl]amino}benzonitrile

生成物 1

HCID 694460384-{N-[(6-hydroxy-benzothien-3-yl)methyl]-N-[1H-imidazol-1-yl-]amino}benzonitrile収率 62.3%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

A solution of 4-{N-[1H-imidazol-1-yl]-N-[(6-methoxy-benzothien-3-yl)methyl]amino}benzonitrile (0.50 g, 1.39 mmol) in 10 ml of methylene chloride is added at room temperature to a solution 1M of boron tribromide in methylene chloride (1.50 ml, 1.52 mmol). After 2 h at room temperature the mixture was hydrolysed with saturated aqueous NaHCO3, extracted with dichloromethane, dried over Na2SO4, filtered, and concentrated in vacuum. The crude product was purified by flash chromatography on silica gel (toluene/dioxan:6/4) to give the expected product (0.30 g, 62%, powder). Crystallization with ethanol yielded white crystalsl (0.10 g, mp: 169° C.).

後処理

  1. extractionextracted with dichloromethane
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuum
  5. customThe crude product was purified by flash chromatography on silica gel (toluene/dioxan:6/4)

出典と根拠

ORDレコード
ord-c315a170c60149839f53f5eb2a0326d2
出典データセット
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08476455B2

反応ノート

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