Acetic Acid → HCID 14008816, compound

HRID 1248099Notes

Reaction equation

HRID 1248099 reaction equation
Br.C(O)(=O)C.C1(=O)[N:10]([CH2:11][C:12]2[N:13]=[C:14]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[O:15][C:16]=2[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)C(=O)C2=CC=CC=C12.[OH-].[Na+]>O>[NH2:10][CH2:11][C:12]1[N:13]=[C:14]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[O:15][C:16]=1[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 260Hydrogen BromideHCID 14798Sodium HydroxideHCID 151064332-[(2,5-Diphenyl-1,3-oxazol-4-yl)methyl]-1H-isoindole-1,3(2H)-dione

Product 1

HCID 14008816HCID 14008816, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture made up of 20 ml of 48% hydrobromic acid, 20 ml of glacial acetic acid and 10 g of 4-phthalimidomethyl-2,5-diphenyloxazole, was heated under reflux until a clear solution resulted (3 hrs.). The solvent was pulled off under vacuum until dryness. The residue was dissolved in 100 ml of water, made basic with 1N NaOH and extracted with ethyl acetate. The ethyl acetate solution was washed with water until neutral and dried over sodium sulfate. The solvent was pulled off under vacuum and the residue was recrystallized from ethyl acetate and hexane.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux until a clear solution
  3. customresulted (3 hrs.)
  4. extractionextracted with ethyl acetate
  5. washThe ethyl acetate solution was washed with water until neutral and
  6. dry with materialdried over sodium sulfate
  7. customthe residue was recrystallized from ethyl acetate and hexane

Sources & evidence

ORD record
ord-c97591e8cfe942bd9fdc29b91f138ab2
Source dataset
uspto-grants-1985_06
Patent number
US04522742

Reaction notes

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