Water → HCID 21486055, compound

HRID 1414913Notes

Reaction equation

HRID 1414913 reaction equation
[C:1]1(=O)[CH2:6][CH2:5][CH2:4][C:3](=[O:7])[CH2:2]1.[C:9]([NH:13][C:14]([NH2:16])=[O:15])([CH3:12])([CH3:11])[CH3:10].O>C1C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>[C:9]([NH:13][C:14]([NH:16][C:1]1[CH2:6][CH2:5][CH2:4][C:3](=[O:7])[CH:2]=1)=[O:15])([CH3:12])([CH3:11])[CH3:10]

Participants

6

Reactant 3

HCID 962WaterHCID 104341,3-CyclohexanedioneHCID 14233(1,1-Dimethylethyl)urea

Product 1

HCID 21486055HCID 21486055, compoundYield 66.7%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 241BenzeneSolvent

Procedure

To a solution of 11.2 g of 1,3-cyclohexanedione in 250 ml of benzene is added 11.6 g tert-butylurea and 100 mg of p-toluenesulfonic acid. The solution is heated at reflux under nitrogen with water removal for three hours. At the end of this period the solution is cooled and the precipitated product removed by filtration. The precipitate is recrystallized from acetonitrile to give 14 g of 1-tert-butyl-3-(3-oxo-1-cyclohexene-1-yl)urea, m.p. 223°-225° C.

Workup

  1. temperatureThe solution is heated
  2. temperatureAt the end of this period the solution is cooled
  3. customthe precipitated product removed by filtration
  4. customThe precipitate is recrystallized from acetonitrile

Sources & evidence

ORD record
ord-8431755f137a43b69ed8b570e3c7ee3b
Source dataset
uspto-grants-1977_01
Patent number
US04002767

Reaction notes

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