Nitrobenzene → Carbanilide
Reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)([O-])=O.C[N:11]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:12](=O)[O-:13]>>[C:4]1([NH:1][C:12]([NH:11][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[O:13])[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1Participants
3
Conditions
- Temperature
- 135 °C
Procedure
The experiment as described in Example 10 was repeated at a temperature of 110° C. using nitrobenzene (7.5 ml) and aniline (4 ml) as feed. Gas-liquid chromatography indicated that the initial amount of aniline had been converted completely and that 1,3-diphenylurea had been formed in high yield (90%, based on aniline. Methyl carbanilate had been obtained in 60% yield, based on nitrobenzene with a nitrobenzene conversion of about 70%). The reaction temperature was then raised to 135° C. and the reaction was allowed to proceed at that temperature for another 5 hours. The total conversion of nitrobenzene amounted to 90% and more methylcarbanilate had been formed, corresponding to the amount of 1,3-diphenylurea converted.
Sources & evidence
- ORD record
- ord-0076306968364dfb864614e5c064482d
- Source dataset
- uspto-grants-1984_10
- Patent number
- US04474978
Reaction notes
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