Benzylamine → HCID 69497767, compound

HRID 460653Notes

Reaction equation

HRID 460653 reaction equation
[CH3:1][O:2][C:3]1[CH:16]=[CH:15][CH:14]=[CH:13][C:4]=1[CH:5]=[C:6]1[C:10](=[O:11])O[C:8]([CH3:12])=[N:7]1.[CH2:17]([NH2:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C([O-])(=O)C.[Na+].C(=O)([O-])[O-].[K+].[K+]>C(O)(=O)C>[CH2:17]([N:24]1[C:10](=[O:11])[C:6](=[CH:5][C:4]2[CH:13]=[CH:14][CH:15]=[CH:16][C:3]=2[O:2][CH3:1])[N:7]=[C:8]1[CH3:12])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 7504BenzylamineHCID 11430Potassium CarbonateHCID 361416HCID 361416, compoundHCID 517045Sodium Acetate

Product 1

HCID 69497767HCID 69497767, compoundYield 19.6%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

4-(2′-Methoxybenzylidene)-2-methyl-4H-oxazol-5-one (5 g) was dissolved in acetic acid (50 ml) and benzylamine (2.68 g) and sodium acetate (2 g) were added. The mixture was heated at 100° C. for 2 hr, poured into ice-water, neutralized with potassium carbonate and extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (1.38 g) as yellow crystals.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-73c781f8153d43b7812d1a931714500e
Source dataset
uspto-grants-2007_03
Patent number
US07196199B2

Reaction notes

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