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

HRID 1070060Notes

Reaction equation

HRID 1070060 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-9cd42e1797b740298216b5ddeb00115d
Source dataset
uspto-grants-2001_06
Patent number
US06251926B1

Reaction notes

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