Urea → HCID 58089233, compound

HRID 251386Notes

Reaction equation

HRID 251386 reaction equation
[CH2:1]([C:6]1[CH:14]=[C:10]([C:11](O)=[O:12])[C:9]([OH:15])=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH2:4][CH3:5].C(N)([NH2:18])=O>CCOC(C)=O>[CH2:1]([C:6]1[CH:14]=[C:10]([C:11]([NH2:18])=[O:12])[C:9]([OH:15])=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

4

Reactant 2

HCID 1176UreaHCID 29078142HCID 29078142, compound

Product 1

HCID 58089233HCID 58089233, compoundYield 51.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

18 g compound 19 (86 mmole), 20.8 g ureum (346 mmole) and 5 drops polyphosphoric acid were heated at 150° C. during 18 h. After cooling, 500 ml EtOAc was added and the resulting solution was washed twice with brine. After evaporation of the organic phase, the resulting residue was purified by flash chromatography (Acros Silicagel 0.060-0.200 mm) using cyclohexane/isopropanol 95:5, affording compound 20 as a white powder (9.17 g, 51% yield).

Workup

  1. temperatureAfter cooling
  2. washthe resulting solution was washed twice with brine
  3. customAfter evaporation of the organic phase
  4. customthe resulting residue was purified by flash chromatography (Acros Silicagel 0.060-0.200 mm)

Sources & evidence

ORD record
ord-7284b8516f8b4b01a7035d4680ac6e20
Source dataset
uspto-grants-2011_01
Patent number
US07863428B2

Reaction notes

Loading…