HCID 11080078, compound → HCID 11761314, compound

HRID 1377641Notes

Reaction equation

HRID 1377641 reaction equation
[OH:1][CH:2]([CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH2:18][C:19]2[N:20]=[C:21]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[O:22][C:23]=2[CH3:24])=[CH:12][CH:11]=1)[C:3](OCC)=[O:4].[O-:31][C:32]#[N:33].[K+]>C(O)CCC>[CH3:24][C:23]1[O:22][C:21]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[N:20][C:19]=1[CH2:18][CH2:17][O:16][C:13]1[CH:14]=[CH:15][C:10]([CH2:9][CH2:8][CH:2]2[O:1][C:32](=[O:31])[NH:33][C:3]2=[O:4])=[CH:11][CH:12]=1

Participants

4

Reactant 2

HCID 11080078HCID 11080078, compoundHCID 11378442Potassium cyanate

Product 1

HCID 11761314HCID 11761314, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A mixture of ethyl 2-hydroxy-4-[4-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]phenyl]butyrate (0.45 g), powdery potassium cyanate (0.24 g) and butanol (20 ml) was heated for 4 days under reflux. The solvent was distilled off under reduced pressure, and the residue was acidified with 2N HCl, followed by extraction with ethyl acetate. The ethyl acetate layer was washed with water, dried (MgSO4), and concentrated. The concentrate was purified by means of a silica gel column chromatography. From the fractions eluted with chloroform-methanol (100:3) was obtained 5-[2-[4-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]phenyl]ethyl]-2,4-oxazolidinedione (0.28 g, 63%). The product was recrystallized from dichloromethane-ethanol to give colorless prisms, m.p.193°-194° C.

Workup

  1. temperaturewas heated for 4 days
  2. temperatureunder reflux
  3. distillationThe solvent was distilled off under reduced pressure
  4. extractionfollowed by extraction with ethyl acetate
  5. washThe ethyl acetate layer was washed with water
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated
  8. customThe concentrate was purified by means of a silica gel column chromatography
  9. washFrom the fractions eluted with chloroform-methanol (100:3)

Sources & evidence

ORD record
ord-fa5e80f60c304b689d8ead89bd51cbad
Source dataset
uspto-grants-1997_09
Patent number
US05665748

Reaction notes

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