N,N-Dimethylaniline → N-[2,4-dibromo-6-methylpyridin-3-yl]-2-bromoacetamide

HRID 227516ノート

反応式

HRID 227516 の反応式
[NH2:1][C:2]1[C:3]([Br:10])=[N:4][C:5]([CH3:9])=[CH:6][C:7]=1[Br:8].CN(C)C1C=CC=CC=1.[Br:20][CH2:21][C:22](Br)=[O:23]>C(Cl)Cl>[Br:10][C:3]1[C:2]([NH:1][C:22](=[O:23])[CH2:21][Br:20])=[C:7]([Br:8])[CH:6]=[C:5]([CH3:9])[N:4]=1

参加物

5

反応物 3

HCID 949N,N-DimethylanilineHCID 61147Bromoacetyl bromideHCID 100842382,4-Dibromo-6-methylpyridin-3-amine

生成物 1

HCID 10430271N-[2,4-dibromo-6-methylpyridin-3-yl]-2-bromoacetamide収率 85.3%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

3-Amino-2,4-dibromo-6-methylpyridine (1.16 g, 4.38 mmol) was dissolved in methylene chloride (10 mL). N,N-dimethylaniline (0.77 g, 6.35 mmol) was added to the solution and then a solution of bromoacetyl bromide (1.03 g, 5.12 mmol) in dichloromethane (2 mL) was added dropwise thereto over 5 minutes with stirring and cooling with ice. After completion of addition, the temperature of the mixture was elevated to room temperature and stirred for 12 hours. The resultant mixture was washed sequentially with water, an aqueous saturated sodium hydrogencarbonate solution, and saturated brine. Subsequently, the mixture was dried over sodium sulfate anhydrate and concentrated under reduced pressure. The residue was crystallized from hexane-acetone, to thereby yield 1.44 g of N-[2,4-dibromo-6-methylpyridin-3-yl]-2-bromoacetamide as colorless crystals (yield 85.3%).

後処理

  1. temperaturecooling with ice
  2. additionAfter completion of addition
  3. customwas elevated to room temperature
  4. stirringstirred for 12 hours
  5. washThe resultant mixture was washed sequentially with water
  6. dry with materialSubsequently, the mixture was dried over sodium sulfate anhydrate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was crystallized from hexane-acetone

出典と根拠

ORDレコード
ord-e10d395fd8334f6f9e4c64dd0960b3fe
出典データセット
uspto-grants-2009_07
特許番号
US07560547B2

反応ノート

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