Toluene → 1-Phenyl-3-(p-toluenesulfonyl)urea

HRID 5764Notes

Reaction equation

HRID 5764 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:8]1(C)[C:9]([S:14]([N:17]=[C:18]=[O:19])(=[O:16])=[O:15])=[CH:10][CH:11]=[CH:12][CH:13]=1.[C:21]1(C)C=CC=CC=1>>[C:12]1([CH3:21])[CH:13]=[CH:8][C:9]([S:14]([NH:17][C:18]([NH:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[O:19])(=[O:15])=[O:16])=[CH:10][CH:11]=1

Participants

4

Reactant 3

HCID 1140TolueneHCID 6115Aniline2×HCID 2733313o-Toluenesulfonyl Isocyanate

Product 1

HCID 8474151-Phenyl-3-(p-toluenesulfonyl)urea

Conditions

Temperature
90 °C

Procedure

A three-necked flask equipped with a dropping funnel, a thermometer, and a reflux condenser was charged with 18.6 g of aniline and the aniline was dissolved in 200 ml of toluene. While the resultant reaction solution was stirred with a magnetic stirrer, 42.0 g of toluenesulfonylisocyanate were added dropwise from the dropping funnel to the reaction solution. During the stirring, an exothermic reaction occurred and a large amount of white solid was precipitated. The resultant reaction mixture was heated at a temperature of 90° C. for one hour, cooled, and then filtered. White crystals were obtained in an amount of 58.0 g. The crystals had a melting point of 166° C.

Workup

  1. customA three-necked flask equipped with a dropping funnel
  2. customWhile the resultant reaction solution
  3. customDuring the stirring, an exothermic reaction
  4. customa large amount of white solid was precipitated
  5. customThe resultant reaction mixture
  6. temperaturecooled
  7. filtrationfiltered
  8. customWhite crystals were obtained in an amount of 58.0 g

Sources & evidence

ORD record
ord-e4e95021117a431db55e0845d2ecf3fd
Source dataset
uspto-grants-1993_09
Patent number
US05246906

Reaction notes

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