Acetic Acid → HCID 15676108, compound

HRID 974051Notes

Reaction equation

HRID 974051 reaction equation
C(O)(=O)C.[CH3:5][NH:6][C:7]1[N:11]=[C:10]([CH:12]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20]3([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)OCC[O:21]3)[CH:15]=2)[CH3:13])[O:9][N:8]=1>O>[CH3:5][NH:6][C:7]1[N:11]=[C:10]([CH:12]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20](=[O:21])[C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH:15]=2)[CH3:13])[O:9][N:8]=1

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 15676097HCID 15676097, compound

Product 1

HCID 15676108HCID 15676108, compoundYield 59.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To the mixture of acetic acid (16 ml) and water (4 ml) was added 3-methylamino-5-(1-(3-(2-phenyl-1,3-dioxolan-2-yl)phenyl)ethyl)-1,2,4-oxadiazole (0.643 g, 2.44 mmol). After the mixture was stirred at room temperature overnight, the mixture was evaporated under reduced pressure to a residue, which was extracted with dichloromethane after saturated NaHCO3 aq. was added. The extracts were washed with water, dried with anhydrous magnesium sulfate, and evaporated under reduced pressure to a residue, which was chromatographed and recrystallized with ethyl acetate and n-hexane to afford 3-methylamino-5-(1-(3-benzoylphenyl)ethyl)-1,2,4-oxadiazole (0.446 g, 59% yield) as crystalline material: mp 100°-101° C.

Workup

  1. customthe mixture was evaporated under reduced pressure to a residue, which
  2. extractionwas extracted with dichloromethane after saturated NaHCO3 aq.
  3. additionwas added
  4. washThe extracts were washed with water
  5. dry with materialdried with anhydrous magnesium sulfate
  6. customevaporated under reduced pressure to a residue, which
  7. customwas chromatographed
  8. customrecrystallized with ethyl acetate and n-hexane

Sources & evidence

ORD record
ord-ec66f03725874836a626f14f24b8707a
Source dataset
uspto-grants-1991_11
Patent number
US05066666

Reaction notes

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