Urea → N-(2-propylpentanoyl)urea

HRID 83977

Reaction equation

HRID 83977 reaction equation
[C:1](Cl)(=[O:9])[CH:2]([CH2:6][CH2:7][CH3:8])[CH2:3][CH2:4][CH3:5].S(Cl)(Cl)=O.C(O)(=O)C(CCC)CCC.[NH2:25][C:26]([NH2:28])=[O:27]>C(#N)C>[CH2:3]([CH:2]([CH2:6][CH2:7][CH3:8])[C:1]([NH:25][C:26]([NH2:28])=[O:27])=[O:9])[CH2:4][CH3:5]

Participants

6

Reactant 4

HCID 1176UreaHCID 3121Valproic AcidHCID 24386Thionyl ChlorideHCID 762402-Propylvaleryl chloride

Product 1

HCID 80191N-(2-propylpentanoyl)urea

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

Valproyl chloride (0.057 mol), prepared by coupling of thionylchloride and valproic acid according to a published method [24], was dissolved in dry acetonitrile (50 ml), and the resulting solution was slowly added to a boiling solution of urea (0.14 mole) in dry acetonitrile (100 ml) and allowed to reflux for 2 hours. Thereafter the organic solvent was evaporated under reduced pressure and the product was dissolved in ethyl acetate (100 ml) and washed three times with 20 ml of distilled water. The organic fraction was dried over MgSO4, filtered and evaporated under reduced pressure. The products were purified by crystallization from ethyl acetate.

Workup

  1. temperatureto reflux for 2 hours
  2. customThereafter the organic solvent was evaporated under reduced pressure
  3. dissolutionthe product was dissolved in ethyl acetate (100 ml)
  4. washwashed three times with 20 ml of distilled water
  5. dry with materialThe organic fraction was dried over MgSO4
  6. filtrationfiltered
  7. customevaporated under reduced pressure
  8. customThe products were purified by crystallization from ethyl acetate

Sources & evidence

ORD record
ord-b43ccd2aa5be4a4bb1e813a1bc026e6d
Source dataset
uspto-grants-2014_09
Patent number
US08846903B2

Linked notes

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