Ethyl isocyanate → 1-Ethyl-3-(3-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)urea

HRID 1626658ノート

反応式

HRID 1626658 の反応式
[F:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[B:9]1[O:13][C:12]([CH3:15])([CH3:14])[C:11]([CH3:17])([CH3:16])[O:10]1)[NH2:5].[CH2:18]([N:20]=[C:21]=[O:22])[CH3:19].[N-]=C=O>C(Cl)Cl>[CH2:18]([NH:20][C:21]([NH:5][C:4]1[CH:6]=[CH:7][C:8]([B:9]2[O:13][C:12]([CH3:15])([CH3:14])[C:11]([CH3:17])([CH3:16])[O:10]2)=[C:2]([F:1])[CH:3]=1)=[O:22])[CH3:19]

参加物

5

反応物 3

HCID 8022Ethyl isocyanateHCID 105034IsocyanateHCID 447552073-Fluoro-4-(tetramethyl-1,3,2-dioxaborolan-2-yl)aniline

生成物 1

HCID 666787871-Ethyl-3-(3-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)urea収率 54%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
35 °C

実験手順

To a stirred solution of 3-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (1.5 g, 6.33 mmol) in DCM (30 ml) was added ethyl isocyanate (1503 μL, 19 mmol). Reaction mixture was stirred at 35° C. for 20 hours. Additional isocyanate was added and reaction mixture left for sufficient time to ensure reaction completion. The crude reaction mixture was then partitioned between water and DCM. The organic layer was recovered, passed through a hydrophobic frit and the solvent removed in vacuo. The residue was purified by flash chromatography using 0-60% ethyl acetate/petroleum ether 40-60 to yield a yellow solid (1.054 g, 3.42 mmol, 54%).

後処理

  1. customReaction mixture
  2. customreaction mixture
  3. waitleft for sufficient time
  4. customreaction completion
  5. customThe crude reaction mixture
  6. customwas then partitioned between water and DCM
  7. customThe organic layer was recovered
  8. customthe solvent removed in vacuo
  9. customThe residue was purified by flash chromatography

出典と根拠

ORDレコード
ord-00e47ba574064dfa8b03abd951223435
出典データセット
uspto-grants-2014_07
特許番号
US08785457B2

反応ノート

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