Urea → Capuride

HRID 83975Notes

Reaction equation

HRID 83975 reaction equation
[CH2:1]([CH:3]([CH:7]([CH3:10])[CH2:8][CH3:9])[C:4](Cl)=[O:5])[CH3:2].S(Cl)(Cl)=O.[NH2:15][C:16]([NH2:18])=[O:17]>C(#N)C>[CH2:1]([CH:3]([CH:7]([CH3:10])[CH2:8][CH3:9])[C:4]([NH:15][C:16]([NH2:18])=[O:17])=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 1176UreaHCID 24386Thionyl ChlorideHCID 247407702-Ethyl-3-methyl-pentanoylchloride2×

Product 1

HCID 231285Capuride

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

2-Ethyl-3-methyl-pentanoylchloride (0.057 mol), was prepared using thionylchloride according to a published method [24], and dissolved in dry acetonitrile (50 ml). The 2-ethyl-3-methyl-pentanoylchloride solution was slowly added to a boiling solution of urea (0.14 moles) in dry acetonitrile (100 ml) and was allowed to reflux for 2 hours. Thereafter the organic solvent was evaporated under reduced pressure and the product was dissolved in 100 ml ethyl acetate and washed three times with 20 ml of distilled water. The organic fraction was dried over MgSO4, filtered and evaporated under reduced pressure. The product was 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 100 ml ethyl acetate
  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 product was purified by crystallization from ethyl acetate

Sources & evidence

ORD record
ord-4a49ac6d765b49f9b31ca0743b96f60c
Source dataset
uspto-grants-2014_09
Patent number
US08846903B2

Reaction notes

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