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

HRID 446167ノート

反応式

HRID 446167 の反応式
Cl[CH2:2][C:3]1[C:7]2[CH:8]=[CH:9][C:10]([O:12][CH3:13])=[CH:11][C:6]=2[S:5][CH:4]=1.[N:14]1([NH:19][C:20]2[CH:27]=[CH:26][C:23]([C:24]#[N:25])=[CH:22][CH:21]=2)[CH:18]=[CH:17][N:16]=[CH:15]1.C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C.[I-].[K+]>[N:14]1([N:19]([C:20]2[CH:21]=[CH:22][C:23]([C:24]#[N:25])=[CH:26][CH:27]=2)[CH2:2][C:3]2[C:7]3[CH:8]=[CH:9][C:10]([O:12][CH3:13])=[CH:11][C:6]=3[S:5][CH:4]=2)[CH:18]=[CH:17][N:16]=[CH:15]1

参加物

7

反応物 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 218271913-Chloromethyl-6-methoxy-benzothiopheneHCID 230181884-[(1H-imidazol-1-yl)amino]benzonitrile

生成物 1

HCID 694453164-{N-[1H-imidazol-1-yl]-N-[(6-methoxy-benzothien-3-yl)methyl]amino}benzonitrile収率 55.2%

試薬・触媒・溶媒 2

HCID 4875Potassium Iodide触媒HCID 6228Dimethylformamide溶媒

実験手順

3-Chloromethyl-6-methoxy-benzothiophene (12.35 g, 58.06 mmol) was added to a mixture of 4[N-(1H-imidazol-1-yl)amino]benzonitrile (9.72 g, 52.78 mmol), K2CO3 (14.60 g, 105.56 mmol) and potassium iodide (0.10 g, 0.60 mmol) in dry DMF (70 ml) at room temperature. The mixture was then stirred at room temperature overnight and after poured into water and extracted with ethyl acetate, dried over Na2SO4, filtered, and concentrated under vacuum to give the crude product as solid (14.30 g). Flash chromatography on silica gel (toluene/dioxan: 6/4) yielded the expected product (10.50 g, 55%, powder).

後処理

  1. extractionextracted with ethyl acetate
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under vacuum
  5. customto give the crude product as solid (14.30 g)

出典と根拠

ORDレコード
ord-807e6a9269684bc09ecb1d12b9da681a
出典データセット
uspto-grants-2013_07
特許番号
US08476455B2

反応ノート

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