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Water → 2-Bromo-N-(4-methoxybenzyl)acetamide

HRID 1009463
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HRID 1009463 반응식
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7][NH2:8])=[CH:5][CH:4]=1.[Br:11][CH2:12][C:13](Br)=[O:14].C(N(CC)CC)C.O>C(Cl)Cl>[Br:11][CH2:12][C:13]([NH:8][CH2:7][C:6]1[CH:9]=[CH:10][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)=[O:14]
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참가 물질

6

반응물 4

HCID 962WaterHCID 8471TriethylamineHCID 61147Bromoacetyl bromideHCID 754524-Methoxybenzylamine

생성물 1

HCID 467366912-Bromo-N-(4-methoxybenzyl)acetamide수율 43.8%

시약·촉매·용매 1

HCID 6344Dichloromethane용매3회

실험 절차

7.42 g of 4-methoxybenzylamine was dissolved in 70 mL of methylene chloride, and a solution (10 mL) of 23.2 g of bromoacetyl bromide in methylene chloride was added thereto at −10° C. To the reaction liquid was added dropwise a solution (10 mL) of 8.0 mL of triethylamine in methylene chloride at 0° C., followed by stirring at room temperature for 30 minutes. To the reaction liquid was added water under ice-cooling, followed by extraction with methylene chloride. The organic layer was washed with an aqueous saturated sodium hydrogen carbonate solution, and then dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=90:10 to 0:100) to obtain a product, which was recrystallized from ethyl acetate to obtain 6.11 g of 2-bromo-N-(4-methoxybenzyl)acetamide.

후처리

  1. customat −10° C
  2. customTo the reaction liquid
  3. customTo the reaction liquid
  4. temperaturecooling
  5. extractionfollowed by extraction with methylene chloride
  6. washThe organic layer was washed with an aqueous saturated sodium hydrogen carbonate solution
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customThe solvent was evaporated under reduced pressure
  9. customthe obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=90:10 to 0:100)
  10. customto obtain a product, which
  11. customwas recrystallized from ethyl acetate

출처 및 근거

ORD 기록
ord-1560ad2b7e8c45cda84cbee322211730
출처 데이터셋
uspto-grants-2011_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07973078B2

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