p-Toluenesulfonic acid → Daimuron

HRID 483270Notes

Reaction equation

HRID 483270 reaction equation
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([NH:7][C:8]([NH2:10])=[O:9])=[CH:3][CH:2]=1.C(#N)C.[C:15]1(C)[CH:20]=CC(S(O)(=O)=O)=C[CH:16]=1.[CH3:26][C:27]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[CH2:28]>CCCCCC>[C:4]1([N:7]([CH:15]([CH3:20])[CH3:16])[C:8]([NH2:10])=[O:9])[CH:3]=[CH:2][CH:1]=[CH:6][CH:5]=1.[CH3:26][C:27]([NH:10][C:8]([NH:7][C:4]1[CH:5]=[CH:6][C:1]([CH3:11])=[CH:2][CH:3]=1)=[O:9])([CH3:28])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

7

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 6342AcetonitrileHCID 7407Alpha-MethylstyreneHCID 12148N-(4-Methylphenyl)urea

Product 2

HCID 39238DaimuronHCID 30321341-Isopropyl-1-phenylurea

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Conditions

Temperature
55 °C

Procedure

A phenylisopropylurea derivative was prepared in accordance with the method of Example 1, as follows: 1.5 parts of N-(p-tolyl)urea was suspended in 3.93 parts of acetonitrile at 55°, and 0.3 parts of p-toluene-sulfonic acid was added. After 1 minute, 4.7 parts of α-methylstyrene were added. The reactants were stirred at 55° C. for 18 hours. After cooling to ambient temperature, 60 parts of hexane was added and the precipitated solid collected, washed with hexane and recrystallized from methylene chloride to afford 2.2 parts of N-(α,α,-dimethylbenzyl)-N'-(p-tolyl)urea.

Workup

  1. temperatureAfter cooling to ambient temperature
  2. customthe precipitated solid collected
  3. washwashed with hexane
  4. customrecrystallized from methylene chloride

Sources & evidence

ORD record
ord-e85e9b15ba004248bfa23ae6a1ff47b7
Source dataset
uspto-grants-1986_03
Patent number
US04578513

Reaction notes

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