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

HRID 2237638ノート

反応式

HRID 2237638 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-16bfb3d726b34845b0fe20538d53142d
出典データセット
uspto-grants-2010_05
特許番号
US07718676B2

反応ノート

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