Ethanol → 4-(2-Phenyl-oxazol-4-ylmethoxy)benzaldehyde oxime

HRID 1720037Notes

Reaction equation

HRID 1720037 reaction equation
[C:1]1([C:7]2[O:8][CH:9]=[C:10]([CH2:12][O:13][C:14]3[CH:21]=[CH:20][C:17]([CH:18]=O)=[CH:16][CH:15]=3)[N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(O)C.N1C=CC=CC=1.Cl.[NH2:32][OH:33]>O>[C:1]1([C:7]2[O:8][CH:9]=[C:10]([CH2:12][O:13][C:14]3[CH:21]=[CH:20][C:17]([CH:18]=[N:32][OH:33])=[CH:16][CH:15]=3)[N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 1049PyridineHCID 443297Hydroxyamine hydrochlorideHCID 108265134-(2-Phenyl-4-oxazolylmethoxy)benzaldehyde

Product 1

HCID 851876084-(2-Phenyl-oxazol-4-ylmethoxy)benzaldehyde oximeYield 97.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
25 °C

Procedure

A solution of 4-(2-phenyl-oxazol-4-ylmethoxy)benzaldehyde (4.3 g, 15.3 mmol), ethanol (100 mL), pyridine (45 mL) and hydroxylamine hydrochloride (2.2 g, 30.8 mmol) was refluxed for 1.5 hours. The solution is cooled to 25° C. and poured into water (600 mL). The resultant precipitate was filtered and dried at 25° C. for 18 hours to give the product as a white solid in 97.1% yield, m.p. 184°-186° C. MS (EI, m/e): 294 (M)+.

Workup

  1. filtrationThe resultant precipitate was filtered
  2. customdried at 25° C. for 18 hours

Sources & evidence

ORD record
ord-108f86ff92924a78987744c37fa2eebf
Source dataset
uspto-grants-1996_04
Patent number
US05504097

Reaction notes

Loading…