Benzene → Fenuron

HRID 1764159Notes

Reaction equation

HRID 1764159 reaction equation
[N+:1]([C:4]1C=CC=CC=1)([O-])=O.[CH3:10][NH2+:11](=S)[CH3:12].[CH:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[C]=[O:21]>>[CH3:10][N:11]([CH3:12])[C:4]([NH:1][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:21]

Participants

4

Reactant 3

HCID 241BenzeneHCID 7416NitrobenzeneHCID 178418416HCID 178418416, compound2×

Product 1

HCID 7560Fenuron

Conditions

Temperature
110 °C

Procedure

A 1/2-liter autoclave was charged with nitrobenzene (30.0 g.), dimethylammonium sulphide (40 g.) benzene (60 g.) and carbon monoxide to a pressure of 50 atmospheres. The temperature of the autoclave was raised to 110° C and its contents were maintained at this temperature with stirring for 21/2 hours. The pressure was renewed to 50 atmospheres at intervals as required by passing in more carbon monoxide. The contents of the autoclave were then allowed to cool below 70° C before being removed and distilled to separate the volatiles, which included unreacted nitrobenzene. The residue, weighing 16 g., was recrystallised from a mixture of benzene and 60-80 petroleum ether to give 1,1-dimethyl-3-phenylurea (12.3 g.).

Workup

  1. temperatureits contents were maintained at this temperature
  2. temperatureto cool below 70° C
  3. custombefore being removed
  4. distillationdistilled
  5. customto separate the volatiles, which
  6. custom, was recrystallised from a mixture of benzene and 60-80 petroleum ether

Sources & evidence

ORD record
ord-0e09b19960e246d9b8c15a13d5706356
Source dataset
uspto-grants-1978_09
Patent number
US04115445

Reaction notes

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