Hydrochloric Acid → 4-(5-Methyl-2-phenyl-oxazol-4-ylmethoxy)-benzaldehyde oxime

HRID 1720035Notes

Reaction equation

HRID 1720035 reaction equation
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][O:14][C:15]1[CH:22]=[CH:21][C:18]([CH:19]=O)=[CH:17][CH:16]=1.Cl.[NH2:24][OH:25].C([O-])(=O)C.[Na+].Cl>C(O)C.O>[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][O:14][C:15]1[CH:22]=[CH:21][C:18]([CH:19]=[N:24][OH:25])=[CH:17][CH:16]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 107561164-(5-Methyl-2-phenyl-4-oxazolyl)methoxybenzaldehyde

Product 1

HCID 852817284-(5-Methyl-2-phenyl-oxazol-4-ylmethoxy)-benzaldehyde oximeYield 89.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

In to a solution of 4-(5-methyl-2-phenyl-oxazol-4-ylmethoxy)-benzaldehyde (6.5 g, 22.2 mmol) in ethanol (300 mL) were added hydroxylamine hydrochloride (4.62 g, 66.55 mmol) and a solution of sodium acetate (7.27 g, 82.7 mmol) in H2O (40 mL). The mixture was stirred at room temperature for 12 h, then poured into H2O, acidified with 1N HCl and extracted with EtOAc. The organic extracts were dried over MgSO4. Evaporation and crystallization from acetone/ether/hexane, gave a white solid (6.1 g, 89% yield, m.p. 192°-193° C.). Analysis for: C18H16N2O3Calc'd: C, 70.12; H, 5.23; N, 9.09 Found: C, 70.31; H, 5.27; N, 8.82

Workup

  1. extractionextracted with EtOAc
  2. dry with materialThe organic extracts were dried over MgSO4
  3. customEvaporation and crystallization from acetone/ether/hexane

Sources & evidence

ORD record
ord-0e376de5591f4cee80afdaa0cfe84e7f
Source dataset
uspto-grants-1996_04
Patent number
US05504097

Reaction notes

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