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

HRID 446168
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HRID 446168 반응식
[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
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참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

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.).

후처리

  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)

출처 및 근거

ORD 기록
ord-c315a170c60149839f53f5eb2a0326d2
출처 데이터셋
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08476455B2

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