Hydrochloric Acid → 5-[4-[2-[5-Methyl-2-(3-methylphenyl)-4-oxazolyl]ethoxy]cinnamylidene]-2,4-oxazolidinedione

HRID 1740896Notes

Reaction equation

HRID 1740896 reaction equation
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([CH3:13])[CH:8]=2)=[N:4][C:3]=1[CH2:14][CH2:15][O:16][C:17]1[CH:26]=[CH:25][C:20](/[CH:21]=[CH:22]/[CH:23]=O)=[CH:19][CH:18]=1.[O:27]1[CH2:31][C:30](=[O:32])[NH:29][C:28]1=[O:33].N1CCCCC1.Cl>O.C(O)C>[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([CH3:13])[CH:8]=2)=[N:4][C:3]=1[CH2:14][CH2:15][O:16][C:17]1[CH:18]=[CH:19][C:20]([CH:21]=[CH:22][CH:23]=[C:31]2[O:27][C:28](=[O:33])[NH:29][C:30]2=[O:32])=[CH:25][CH:26]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8082PiperidineHCID 973892,4-OxazolidinedioneHCID 15485649(E)-4-[2-[5-methyl-2-(3-methylphenyl)-4-oxazolyl]ethoxy]cinnamaldehyde

Product 1

HCID 570370095-[4-[2-[5-Methyl-2-(3-methylphenyl)-4-oxazolyl]ethoxy]cinnamylidene]-2,4-oxazolidinedioneYield 34.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A mixture of (E)-4-[2-[5-methyl-2-(3-methylphenyl)-4-oxazolyl]ethoxy]cinnamaldehyde (1.20 g), 2,4-oxazolidinedione (0.525 g), piperidine (0.09 g) and ethanol (20 ml) was heated for 5 hours under reflux. The reaction mixture was poured into water, which was acidified with 2N HCl, followed by extraction with ethyl acetate. The ethyl acetate layer was washed with water, dried (MgSO4) and, then, concentrated. The concentrate was purified by means of a silica gel column chromatography. From the fractions eluted with chloroform-methanol (50:1) was obtained 5-[4-[2-[5-methyl-2-(3-methylphenyl)-4-oxazolyl]ethoxy]cinnamylidene]-2,4-oxazolidinedione (0.51 g, 34%). Recrystallization from dichloromethane-methanol gave pale yellow prisms, m.p.213-214° C.

Workup

  1. temperaturewas heated for 5 hours
  2. temperatureunder reflux
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe ethyl acetate layer was washed with water
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. customThe concentrate was purified by means of a silica gel column chromatography
  8. washFrom the fractions eluted with chloroform-methanol (50:1)

Sources & evidence

ORD record
ord-aa505093bb954ccb9d8c7b2961d0be5c
Source dataset
uspto-grants-1999_10
Patent number
US05972970

Reaction notes

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