Potassium Carbonate → 1-(3-Bromophenyl)-2-(diallylamino)ethanone

HRID 77563ノート

反応式

HRID 77563 の反応式
C(=O)([O-])[O-].[K+].[K+].[Br:7][C:8]1[CH:9]=[C:10]([CH:15]=[CH:16][CH:17]=1)[C:11](=[O:14])[CH2:12]Br.[CH2:18]([NH:21][CH2:22][CH:23]=[CH2:24])[CH:19]=[CH2:20]>C(#N)C>[Br:7][C:8]1[CH:9]=[C:10]([C:11](=[O:14])[CH2:12][N:21]([CH2:22][CH:23]=[CH2:24])[CH2:18][CH:19]=[CH2:20])[CH:15]=[CH:16][CH:17]=1

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 31279DiallylamineHCID 5195852-Bromo-1-(3-bromophenyl)ethan-1-one

生成物 1

HCID 867627501-(3-Bromophenyl)-2-(diallylamino)ethanone収率 98%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
0 °C

実験手順

Potassium carbonate (38.8 g, 281 mmol) is added to 3-bromophenacyl bromide (60 g 216 mmol) in acetonitrile (430 mL), and the mixture is cooled under nitrogen to 0° C. Diallylamine (34.6 mL, 280.63 mmol) is added drop wise over 1 hour and the reaction is allowed to warm to 22° C. overnight. The crude reaction mixture is concentrated and the residue is partitioned in water (300 mL) and MTBE (300 mL). The aqueous layer is discarded and the organic layer is washed with water (100 mL, 2×) and with brine (100 mL). The organic layer is dried over sodium sulfate, filtered, and the solvent evaporated to constant weight to give the title compound (62 g, 98%). ES/MS (m/e): 294 (M+1).

後処理

  1. temperatureto warm to 22° C. overnight
  2. customThe crude reaction mixture
  3. concentrationis concentrated
  4. customthe residue is partitioned in water (300 mL)
  5. washthe organic layer is washed with water (100 mL, 2×) and with brine (100 mL)
  6. dry with materialThe organic layer is dried over sodium sulfate
  7. filtrationfiltered
  8. customthe solvent evaporated to constant weight

出典と根拠

ORDレコード
ord-97c2129e07374dcf8c1acfa9497f141a
出典データセット
uspto-grants-2014_09
特許番号
US08841293B1

反応ノート

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