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

HRID 1639707Notes

Reaction equation

HRID 1639707 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

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%).

Workup

  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)

Sources & evidence

ORD record
ord-4f1d817d468c451b99f3916e98a93547
Source dataset
uspto-grants-2012_02
Patent number
US08110591B2

Reaction notes

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