Phosphate → HCID 18698544, compound

HRID 2290035Notes

Reaction equation

HRID 2290035 reaction equation
[OH:1][CH2:2][CH2:3][NH:4][C:5]1[CH:23]=[CH:22][C:8]([NH:9][CH:10]=[C:11]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:7][CH:6]=1.[C:24](N1C=CN=C1)(N1C=CN=C1)=[O:25].C1(C)C=CC=CC=1.P([O-])([O-])([O-])=O>C(OCC)(=O)C>[O:25]=[C:24]1[N:4]([C:5]2[CH:6]=[CH:7][C:8]([NH:9][CH:10]=[C:11]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:22][CH:23]=2)[CH2:3][CH2:2][O:1]1

Participants

6

Reactant 4

HCID 1061PhosphateHCID 1140TolueneHCID 682631,1'-CarbonyldiimidazoleHCID 18698604HCID 18698604, compound

Product 1

HCID 18698544HCID 18698544, compoundYield 88.7%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a flask containing diethyl 2-({4-[(2-hydroxyethyl)amino]anilino}methylene)-malonate (0.48 g) and 1,1'-carbonyldiimidazole (0.32 g) is added toluene (15 mL). The reaction mixture is heated to reflux under an argon atmosphere overnight. The reaction mixture is cooled to room temperatue and partioned between ethyl acetate and phosphate buffer (pH=7, 1M). The phases are separated and the aqueous layer is extracted with two additional portions of ethyl acetate. The combined organic layers are washed with buffer, brine, dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue is chromatographed on silica eluting with ethyl acetate. The product-containing fractions are evaporated to give 0.46 g of diethyl 2-{[4-(2-oxo-1,3-oxazolidin-3-yl)anilino]methylene}malonate as a creme solid.

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureto reflux under an argon atmosphere overnight
  3. temperatureThe reaction mixture is cooled to room temperatue
  4. customThe phases are separated
  5. extractionthe aqueous layer is extracted with two additional portions of ethyl acetate
  6. washThe combined organic layers are washed with buffer, brine
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customThe residue is chromatographed on silica eluting with ethyl acetate
  11. customThe product-containing fractions are evaporated

Sources & evidence

ORD record
ord-46c1513a74c54545b51ab101bf81326f
Source dataset
uspto-grants-2000_07
Patent number
US06093732

Reaction notes

Loading…