Hydrochloric Acid → HCID 70105219, compound

HRID 977233Notes

Reaction equation

HRID 977233 reaction equation
O[CH:2]([C:17]1[CH:22]=[CH:21][C:20]([CH2:23][CH2:24][CH2:25][CH:26]2[O:30][C:29](=[O:31])[NH:28][C:27]2=[O:32])=[CH:19][CH:18]=1)[CH2:3][CH2:4][C:5]1[N:6]=[C:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[O:8][C:9]=1[CH3:10].Cl>O1CCCC1>[CH3:10][C:9]1[O:8][C:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[N:6][C:5]=1[CH2:4][CH:3]=[CH:2][C:17]1[CH:22]=[CH:21][C:20]([CH2:23][CH2:24][CH2:25][CH:26]2[O:30][C:29](=[O:31])[NH:28][C:27]2=[O:32])=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 11761871HCID 11761871, compound

Product 1

HCID 70105219HCID 70105219, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 5-[3-[4-[1-hydroxy-3-(5-methyl-2-phenyl-4-oxazolyl)propyl]phenyl]propyl]-2,4-oxazolidinedione (0.17 g), 9N HCl (10 ml) and tetrahydrofuran (THF) (10 ml) was heated under refluxing conditions for 2 hours. The reaction mixture was concentrated under reduced pressure; the residue was poured over water and extracted with ethyl acetate. The ethyl acetate layer was washed with water, dried (MgSO4) and then concentrated under reduced pressure; the residue was purified by silica gel column chromatography. From the fraction eluted with chloroform-methanol (100:2), 5-[3-[4-[3-(5-methyl-2-phenyl-4-oxazolyl)-1-propenyl]phenyl]propyl]-2,4oxazolidinedione (0.045 g, 28%) was obtained, which was then recrystallized from ether-isopropyl ether to yield colorless needles having a melting point of 136°-137° C.

Workup

  1. temperaturewas heated under refluxing conditions for 2 hours
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. additionthe residue was poured over water
  4. extractionextracted with ethyl acetate
  5. washThe ethyl acetate layer was washed with water
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated under reduced pressure
  8. customthe residue was purified by silica gel column chromatography
  9. washFrom the fraction eluted with chloroform-methanol (100:2)

Sources & evidence

ORD record
ord-3388af7c91694121bed9f15d7b10c57d
Source dataset
uspto-grants-1997_03
Patent number
US05614544

Reaction notes

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