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

HRID 1626658노트

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HRID 1626658 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

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온도
35 °C

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-00e47ba574064dfa8b03abd951223435
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08785457B2

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