Sodium Hydroxide → HCID 10680979, compound

HRID 365069Notes

Reaction equation

HRID 365069 reaction equation
[C:1]([C:4]([NH:9][C:10]([C:12]1[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=1)=O)([CH3:8])[CH:5]([CH3:7])[CH3:6])(=[O:3])[NH2:2].[OH-].[Na+]>O1CCOCC1>[CH:5]([C:4]1([CH3:8])[C:1](=[O:3])[NH:2][C:10]([C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=2)=[N:9]1)([CH3:7])[CH3:6]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 13535921HCID 13535921, compound

Product 1

HCID 10680979HCID 10680979, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 24.8 g (0.10 mol) of N-(1-carbamoyl-1,2-dimethylpropyl)-p-toluamide in 263 mL of a 2N sodium hydroxide solution (0.50 mol NaOH) is heated with 100 mL p-dioxane and heated on a steam bath for 72 hours. The p-dioxane is removed in vacuo and the remaining aqueous solution is cooled to 5°-10° C. After carefully acidifying to pH 3-4 with concentrated sulfuric acid, the reaction mixture is extracted with a total of 750 mL methylene chloride. The organic phase is washed with 200 mL of a saturated sodium chloride solution, dried over magnesium sulfate and evaporated to dryness in vacuo to give a yellow solid residue, weighing 22.1 g. The nmr spectrum is consistent with the desired structure. This compound can be recrystallized from acetonitrile to give analytically pure 4-isopropyl-4-methyl-2-p-tolyl-2-imidazolin-5-one mp 151°-154° C.

Workup

  1. temperatureheated on a steam bath for 72 hours
  2. customThe p-dioxane is removed in vacuo
  3. temperaturethe remaining aqueous solution is cooled to 5°-10° C
  4. extractionthe reaction mixture is extracted with a total of 750 mL methylene chloride
  5. washThe organic phase is washed with 200 mL of a saturated sodium chloride solution
  6. dry with materialdried over magnesium sulfate
  7. customevaporated to dryness in vacuo
  8. customto give a yellow solid residue
  9. customThis compound can be recrystallized from acetonitrile

Sources & evidence

ORD record
ord-1b52739638b74e219ee29e48e736cd26
Source dataset
uspto-grants-1986_08
Patent number
US04608079

Reaction notes

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