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

HRID 1009463
ノート
印刷プレビュー

反応式

HRID 1009463 の反応式
[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]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 962WaterHCID 8471TriethylamineHCID 61147Bromoacetyl bromideHCID 754524-Methoxybenzylamine

生成物 1

HCID 467366912-Bromo-N-(4-methoxybenzyl)acetamide収率 43.8%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒3 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-1560ad2b7e8c45cda84cbee322211730
出典データセット
uspto-grants-2011_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07973078B2

反応ノート

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