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Methyl iodide → N-(4-bromophenyl)-N-methylacetamide

HRID 252995
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HRID 252995 반응식
[H-].[Na+].[Br:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11](=[O:13])[CH3:12])=[CH:6][CH:5]=1.CI.[C:16](=O)([O-])O.[Na+]>CN(C)C=O>[Br:3][C:4]1[CH:5]=[CH:6][C:7]([N:10]([CH3:16])[C:11](=[O:13])[CH3:12])=[CH:8][CH:9]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 6328Methyl iodideHCID 76834'-BromoacetanilideHCID 24758Sodium hydrideHCID 516892Sodium Bicarbonate

생성물 1

HCID 4324567N-(4-bromophenyl)-N-methylacetamide수율 90%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

Sodium hydride (101.5 mg, 2.33 mmol) (55% in paraffin liquid) was added to a solution of 249 mg (1.16 mmol) of the title compound produced in step (i) of Reference Example 7 in N,N-dimethylformamide (2.5 ml), and the mixture was stirred at room temperature for 30 min. Thereafter, methyl iodide was added, and the mixture was stirred at room temperature for 1 hr. The reaction was stopped by adding a saturated aqueous sodium hydrogencarbonate solution, and the reaction solution was extracted with ethyl acetate. The organic layer was washed with water and saturated brine in that order, was dried over anhydrous sodium sulfate, and was filtered. The filtrate was concentrated under the reduced pressure, and the residue was purified by column chromatography on silica gel (hexane:ethyl acetate=2:1) to give 239 mg (yield 90%) of the title compound.

후처리

  1. stirringthe mixture was stirred at room temperature for 1 hr
  2. extractionthe reaction solution was extracted with ethyl acetate
  3. washThe organic layer was washed with water and saturated brine in that order
  4. dry with materialwas dried over anhydrous sodium sulfate
  5. filtrationwas filtered
  6. concentrationThe filtrate was concentrated under the reduced pressure
  7. customthe residue was purified by column chromatography on silica gel (hexane:ethyl acetate=2:1)

출처 및 근거

ORD 기록
ord-2965961260a547e0839bf7d84898126b
출처 데이터셋
uspto-grants-2011_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07871982B2

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