Urea → 4-Nitroaniline
Reaction equation
N[C:2]([NH2:4])=O.C(=O)([O-])[O-].[K+].[K+].[OH-].[K+].C1C2C3=C4C(=CC=2)C=CC=C4C=CC3=CC=1.[N+:29]([C:32]1[CH:37]=[CH:36]C=[CH:34][CH:33]=1)([O-:31])=[O:30]>C(OCC)(=O)C.O.CS(C)=O>[N+:29]([C:32]1[CH:37]=[CH:36][C:2]([NH2:4])=[CH:34][CH:33]=1)([O-:31])=[O:30]Participants
Conditions
- Temperature
- 90 °C
Procedure
A 100 ml three-neck reactor equipped with a condenser and a thermometer was filled with 3.60 g (60 mmol) of urea, 1.50 g of potassium carbonate, 3.96 g (60 mmol) of potassium hydroxide, 0.3034 g of pyrene, and 25 g of DMSO. Then, the resulting mixture was heated to 90° C. while stirring under an oxygen atmosphere. Once the reaction temperature reached 90° C., a mixed solution of 2.48 g (20 mmol) of nitrobenzene and 5 g of DMSO was slowly added dropwise over a period of time of 5 to 10 minutes via a syringe. Then, a temperature was cautioned to keep 90±4° C. while adding a nitrobenzene solution. For a quantitative analysis, a sample was taken out and dissolved in 2.5 ml of ethyl acetate containing a small amount of water, and moisture was then removed from the resulting solution with magnesium sulfate (MgSO4). The quantitative analysis has shown that 4-nitrosoaniline and 4-nitroaniline were obtained in yields of 87 mole % and 12 mole %, respectively, based on nitrobenzene.
Workup
- customA 100 ml three-neck reactor equipped with a condenser
- customreached 90° C.
- customto keep 90±4° C.
- customwas then removed from the resulting solution with magnesium sulfate (MgSO4)
Sources & evidence
- ORD record
- ord-9fc22eca6c94420090283bd937c99a4d
- Source dataset
- uspto-grants-2001_03
- Patent number
- US06198001B1
Reaction notes
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