Tetrahydrofuran → 3-(5-Methyl-2-phenyl-4-oxazolylmethoxy)benzyloxyamine

HRID 2299734Notes

Reaction equation

HRID 2299734 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:19]=[C:20]([CH:34]=[CH:35][CH:36]=1)[CH2:21][O:22][N:23]1C(=O)C2=CC=CC=C2C1=O.O1CCCC1.C(=O)([O-])[O-].[K+].[K+]>C(O)C>[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]=[C:20]([CH:34]=[CH:35][CH:36]=1)[CH2:21][O:22][NH2:23]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 11430Potassium CarbonateHCID 24654Hydrazine hydrate (1:1)HCID 11732904N-[3-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyloxy]phthalimide

Product 1

HCID 109249463-(5-Methyl-2-phenyl-4-oxazolylmethoxy)benzyloxyamineYield 97%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Hydrazine monohydrate (0.661 ml) was added to a solution of N-[3-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyloxy]phthalimide (3.00 g) in ethanol (25 ml)-tetrahydrofuran (25 ml) and heated under reflux for 3 hours. The reaction mixture was cooled to room temperature, an aqueous solution of potassium carbonate was added 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 3-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyloxyamine (2.04 g, yield 97%) as pale-yellow crystals. m.p. 81-82° 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-947825858e474b86befa1171c65b5a6b
Source dataset
uspto-grants-2002_12
Patent number
US06495581B1

Reaction notes

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