Urea → HCID 69130644, compound

HRID 2253271Notes

Reaction equation

HRID 2253271 reaction equation
[NH2:1][C:2]([NH2:4])=[O:3].[O-]CC.[Na+].[CH3:9][O:10][C:11]1[CH:12]=[C:13]([CH:19]=[C:20]([C:24]2[CH:29]=[CH:28][C:27]([O:30][C:31]3[CH:36]=[CH:35][C:34]([CH:37]=[CH:38][C:39](OCC)=[O:40])=[CH:33][CH:32]=3)=[CH:26][CH:25]=2)[C:21]([OH:23])=[O:22])[CH:14]=[C:15]([O:17][CH3:18])[CH:16]=1>C(O)C>[CH3:18][O:17][C:15]1[CH:14]=[C:13]([CH:19]=[C:20]([C:24]2[CH:29]=[CH:28][C:27]([O:30][C:31]3[CH:32]=[CH:33][C:34]([CH:37]=[CH:38][C:39](=[O:40])[NH:1][C:2]([NH2:4])=[O:3])=[CH:35][CH:36]=3)=[CH:26][CH:25]=2)[C:21]([OH:23])=[O:22])[CH:12]=[C:11]([O:10][CH3:9])[CH:16]=1

Participants

5

Reactant 3

HCID 1176UreaHCID 2723922Sodium ethoxideHCID 69130598HCID 69130598, compound

Product 1

HCID 69130644HCID 69130644, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Urea (0.21 g, 3.58 mmol) was dissolved in sodium ethoxide (2.7 M, 2.2 mL, 5.92 mmol) at 80° C. under argon, and to this a solution of 4 (1.14 g, 2.37 mmol) in anhydrous ethanol (15 mL) was added and heated at this temperature for 13 hr. Ethanol was evaporated under reduced pressure, water (20 mL) was added, acidified to pH 1 by 5% aqueous HCl and extracted with ethyl acetate (50 mL). The organic layer was washed with water (2×25 mL), brine (2×20 mL), dried over anhydrous magnesium sulfate and evaporated. The crude product was purified by silica gel chromatography and eluted with hexane-ethyl acetate (3:7) containing acetic acid (1%), followed by recrystallization from ethanol. Yield: 167 mg, 14.4%.

Workup

  1. temperatureheated at this temperature for 13 hr
  2. customEthanol was evaporated under reduced pressure, water (20 mL)
  3. additionwas added
  4. extractionextracted with ethyl acetate (50 mL)
  5. washThe organic layer was washed with water (2×25 mL), brine (2×20 mL)
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customevaporated
  8. customThe crude product was purified by silica gel chromatography
  9. washeluted with hexane-ethyl acetate (3:7)
  10. additioncontaining acetic acid (1%)
  11. customfollowed by recrystallization from ethanol

Sources & evidence

ORD record
ord-9046a14d3c4b48d5983027b1cb44d0fb
Source dataset
uspto-grants-2008_01
Patent number
US07323496B2

Reaction notes

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