Toluene → HCID 15538105, compound
Reaction equation
C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:8])C=CC=CC=1.C(OC(=O)C1C=CC(C(O)=O)=C([N+:31]([O-:33])=[O:32])C=1)C.C([N:37]([CH2:40]C)CC)C.[NH2:42][C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1.[C:49]1([CH3:55])[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1>C(OCC)(=O)C>[N+:31]([C:52]1[CH:53]=[CH:54][C:49]([CH3:55])=[CH:50][C:51]=1[NH:37][C:40]([NH:42][C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)=[O:8])([O-:33])=[O:32]Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Procedure
To Diphenylphosphoryl azide (5.75 g) in anhydrous toluene (50 mL) al. 100° C. under nitrogen was added dropwise a solution containing Ethyl-3-nitro-4-carboxybenzoate (5 g) and triethylamine (4 mL) in anhydrous toluene (50 mL). The mixture was stirred for 1 h followed by the addition of aniline (5 mL). and the reaction was allowed to cool to room temperature (40 min). Ethyl acetate (300 mL) was added and the solution was washed successively with 1N HCl (300 mL), water (300 mL), 1N NaOH (300 mL) and water (300 mL). The organic layer was dried and the solvent was removed ill vacuo. To the resulting oil was added diethyl ether (50 mL). and the resulting solid was collected and dried yielding N-(2-Nitro-5-methylphenyl)-N′-phenyl-urea as a white solid.
Workup
- washthe solution was washed successively with 1N HCl (300 mL), water (300 mL), 1N NaOH (300 mL) and water (300 mL)
- customThe organic layer was dried
- customthe solvent was removed ill vacuo
- additionTo the resulting oil was added diethyl ether (50 mL)
- customand the resulting solid was collected
- customdried
Sources & evidence
- ORD record
- ord-82f12b1fcfa1445891c8a7e0c85b744c
- Source dataset
- uspto-grants-2001_07
- Patent number
- US06268496B1
Reaction notes
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