Triphenylphosphine → 4-[2-(2-Methyl-5-nitro-phenylamino)-oxazol-5-yl]-benzonitrile

HRID 244587Notes

Reaction equation

HRID 244587 reaction equation
[N:1]([CH2:4][C:5]([C:7]1[CH:14]=[CH:13][C:10]([C:11]#[N:12])=[CH:9][CH:8]=1)=[O:6])=[N+]=[N-].[CH3:15][C:16]1[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][C:17]=1[N:25]=[C:26]=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCOCC1>[CH3:15][C:16]1[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][C:17]=1[NH:25][C:26]1[O:6][C:5]([C:7]2[CH:14]=[CH:13][C:10]([C:11]#[N:12])=[CH:9][CH:8]=2)=[CH:4][N:1]=1

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 2926092-Methyl-5-nitrophenyl isocyanateHCID 586617294-(2-Azidoacetyl)benzonitrile

Product 1

HCID 248719944-[2-(2-Methyl-5-nitro-phenylamino)-oxazol-5-yl]-benzonitrileYield 45%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 4-Azidoacetyl-benzonitrile (1.5 g, 8.06 mmol) in dioxane 25 mL was added 2-methyl-5-nitrophenyl isocyanate (1.43 mg, 8.06 mmol) (commercially available), and triphenylphosphine (2.11 g, 8.06 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 solid residue was recrystallized from ethanol to give the title compound as yellow micro crystals (1.16 g, 45%).

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
  4. customthe solid residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-b20debc4adc8408c91f43c8192d2d528
Source dataset
uspto-grants-2014_02
Patent number
US08658659B2

Reaction notes

Loading…