Triphenylphosphine → (2-Methyl-5-nitro-phenyl)-(5-pyridin-3-yloxazol-2-yl)-amine

HRID 2237638노트

반응식

HRID 2237638 반응식
[N:1]([CH2:4][C:5]([C:7]1[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=1)=[O:6])=[N+]=[N-].[CH3:13][C:14]1[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][C:15]=1[N:23]=[C:24]=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCOCC1>[CH3:13][C:14]1[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][C:15]=1[NH:23][C:24]1[O:6][C:5]([C:7]2[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=2)=[CH:4][N:1]=1

참가 물질

5

반응물 3

HCID 11776TriphenylphosphineHCID 2926092-Methyl-5-nitrophenyl isocyanateHCID 593028753-Azidoacetylpyridine

생성물 1

HCID 59302880(2-Methyl-5-nitro-phenyl)-(5-pyridin-3-yloxazol-2-yl)-amine수율 78%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

실험 절차

To a solution of 3-azidoacetylpyridine (800 mg, 4.94 mmol) in dioxane 10 mL was added 2-methyl-5-nitrophenyl isocyanate (880 mg, 4.94 mmol) (commercially available), and triphenylphosphine (1.29 g, 4.94 mmol). The reaction mixture was placed in an oil bath preheated to 100° C. and stirred for 30 min. After evaporation of the solvent under reduced pressure the residue was partitioned between 4N HCl (20 mL) and dichloromethane (20 mL). The aqueous layer was neutralized with 15% NaOH and extracted with dichloromethane (3×20 mL). The combined organic layers were washed with brine (20 mL), dried over anhydrous MgSO4, concentrated. The residue was silica gel column chromatographed (dichloromethane/ethanol:97/3) to give the title compound as yellow micro crystals (1.14 g, 78%).

후처리

  1. customThe reaction mixture was placed in an oil bath
  2. custompreheated to 100° C.
  3. customAfter evaporation of the solvent under reduced pressure the residue
  4. customwas partitioned between 4N HCl (20 mL) and dichloromethane (20 mL)
  5. extractionextracted with dichloromethane (3×20 mL)
  6. washThe combined organic layers were washed with brine (20 mL)
  7. dry with materialdried over anhydrous MgSO4
  8. concentrationconcentrated
  9. customchromatographed (dichloromethane/ethanol:97/3)

출처 및 근거

ORD 기록
ord-16bfb3d726b34845b0fe20538d53142d
출처 데이터셋
uspto-grants-2010_05
특허 번호
US07718676B2

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