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

HRID 446167노트

반응식

HRID 446167 반응식
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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 4875Potassium Iodide촉매HCID 6228Dimethylformamide용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-807e6a9269684bc09ecb1d12b9da681a
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08476455B2

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