Toluene → Carbanilide

HRID 658417Notes

Reaction equation

HRID 658417 reaction equation
C1(C)C=CC(S(O)(=O)=[O:8])=CC=1.[NH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[N+:19]([C:22]1C=CC=CC=1)([O-])=O.[C:28]1(C)[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>O>[C:13]1([NH:12][C:22]([NH:19][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[O:8])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

7

Reactant 5

HCID 1140TolueneHCID 6101p-Toluenesulfonic acidHCID 6115AnilineHCID 7416NitrobenzeneHCID 178506046HCID 178506046, compound

Product 1

HCID 7595CarbanilideYield 23.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The above reaction was carried out in a high-grade stainless steel autoclave fitted with a polytetrafluoroethylene beaker of 100 cm3 capacity. 0.0373 g (0.1 mmole) of N,N′-bis(salicylidene)-1,2-phenylenediaminocobalt(II), 0.0172 g (0.1 mmole( of p-toluenesulfonic acid, 4.6498 g (50.0 mmole) aniline, 1.2318 g (10.0 mmole) of nitrobenzene and 8.69 g (10 mmole) of toluene were mixed in the autoclave. The autoclave was flushed three times with gaseous nitrogen and then was pressurized with 50 bar carbon monoxide. After the gas supply was interrupted, the autoclave was inserted into an aluminum block that had been preheated to 200° C. Following 5 minutes, the autoclave reaction temperature reached 170° C. which thereupon was kept constant. Following 6 h of reaction, the autoclave was cooled with cold water and ice and reached room temperature in 5 minutes. The reaction mixture was filtered off and the solid substance so obtained was washed with toluene (3×10 ml). Thereupon the solid substance was dried in high vacuum for 4 h. Characterization was implemented by 1H-NMR, MS, CHN analysis and melting point. This test, not yet optimized, gave 3.0414 g of N,N′-diphenylurea, relating to a yield of 23.9%.

Workup

  1. customThe above reaction
  2. customThe autoclave was flushed three times with gaseous nitrogen
  3. customhad been preheated to 200° C
  4. customreached 170° C.
  5. customFollowing 6 h of reaction
  6. waitreached room temperature in 5 minutes
  7. filtrationThe reaction mixture was filtered off
  8. customthe solid substance so obtained
  9. washwas washed with toluene (3×10 ml)
  10. customThereupon the solid substance was dried in high vacuum for 4 h

Sources & evidence

ORD record
ord-8fb3d369786c4893894885edc66a68d1
Source dataset
uspto-grants-2011_12
Patent number
US08076500B2

Reaction notes

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