Potassium Carbonate → Tert-butyl (3-methyl-4-((5-nitropyridin-2-yl)oxy)phenyl)carbamate

HRID 1844509노트

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HRID 1844509 반응식
[C:1]([O:5][C:6](=[O:16])[NH:7][C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[C:10]([CH3:15])[CH:9]=1)([CH3:4])([CH3:3])[CH3:2].Cl[C:18]1[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][N:19]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH3:15][C:10]1[CH:9]=[C:8]([NH:7][C:6](=[O:16])[O:5][C:1]([CH3:4])([CH3:3])[CH3:2])[CH:13]=[CH:12][C:11]=1[O:14][C:18]1[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][N:19]=1

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 783082-Chloro-5-nitropyridineHCID 22648871tert-butyl N-(4-hydroxy-3-methylphenyl)carbamate

생성물 1

HCID 66980734Tert-butyl (3-methyl-4-((5-nitropyridin-2-yl)oxy)phenyl)carbamate수율 78.1%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
80 °C

실험 절차

To a DMF (50 ml) solution of tert-butyl(4-hydroxy-3-methylphenyl)carbamate (5.00 g) was added 2-chloro-5-nitropyridine (3.91 g) and potassium carbonate (4.64 g). After stirring at 80° C. for 4 hours, the mixture was concentrated under reduced pressure. The residue was diluted in AcOEt and water, and extracted with AcOEt. The organic layer was washed with water, saturated aqueous NaCl, dried over anhydrous Na2SO4 and concentrated under reduced pressure. To the residue were added Et2O and the mixture was stirred at room temperature for 2 hours. The resulting precipitate was collected by filtration to afford the title compound (6.04 g) as a brown powder.

후처리

  1. concentrationthe mixture was concentrated under reduced pressure
  2. additionThe residue was diluted in AcOEt
  3. extractionwater, and extracted with AcOEt
  4. washThe organic layer was washed with water, saturated aqueous NaCl
  5. dry with materialdried over anhydrous Na2SO4
  6. concentrationconcentrated under reduced pressure
  7. additionTo the residue were added Et2O
  8. stirringthe mixture was stirred at room temperature for 2 hours
  9. filtrationThe resulting precipitate was collected by filtration

출처 및 근거

ORD 기록
ord-60458a703f4a4db5855e1a418eb427f7
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08946437B2

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