Tetrahydrofuran → 4-(5-Methyl-2-phenyl4-oxazolylmethoxy)benzyloxyamine

HRID 2299724Notes

Reaction equation

HRID 2299724 reaction equation
O.NN.[CH3:4][C:5]1[O:9][C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[N:7][C:6]=1[CH2:16][O:17][C:18]1[CH:36]=[CH:35][C:21]([CH2:22][O:23][N:24]2C(=O)C3=CC=CC=C3C2=O)=[CH:20][CH:19]=1.O1CCCC1>C(O)C.C(=O)([O-])[O-].[K+].[K+]>[CH3:4][C:5]1[O:9][C:8]([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)=[N:7][C:6]=1[CH2:16][O:17][C:18]1[CH:19]=[CH:20][C:21]([CH2:22][O:23][NH2:24])=[CH:35][CH:36]=1

Participants

6

Reactant 3

HCID 8028TetrahydrofuranHCID 24654Hydrazine hydrate (1:1)HCID 22344648N-[4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyloxy]phthalimide

Product 1

HCID 223445934-(5-Methyl-2-phenyl4-oxazolylmethoxy)benzyloxyamineYield 90.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 11430Potassium CarbonateSolvent

Procedure

Hydrazine monohydrate (1.15 ml) was added to a solution of N-[4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyloxy]phthalimide (5.22 g) in ethanol (40 ml)-tetrahydrofuran (40 ml) and heated under reflux for 3 hours. The reaction mixture was cooled to room temperature, diluted with an aqueous solution of potassium carbonate and extracted with ethyl acetate. The ethyl acetate layer was washed with an aqueous saturated solution of sodium chloride, dried (MgSO4) and concentrated. The remaining crystals were recrystallized from ethyl acetate-hexane to obtain 4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyloxyamine (3.32 g, yield 90%) as colorless crystals. m.p. 68-69° C.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 3 hours
  3. extractionextracted with ethyl acetate
  4. washThe ethyl acetate layer was washed with an aqueous saturated solution of sodium chloride
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. customThe remaining crystals were recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-15a7b399b44543549e306d01d36d3bd2
Source dataset
uspto-grants-2002_12
Patent number
US06495581B1

Reaction notes

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