Hydrochloric Acid → 1-(5-methyl-4-(o-tolyl)-4H-1,2,4-triazol-3-yl)-2-phenylethanone oxime

HRID 1506631Notes

Reaction equation

HRID 1506631 reaction equation
[CH3:1][C:2]1[N:3]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[CH3:22])[C:4]([C:7](=O)[CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[N:5][N:6]=1.Cl.[NH2:24][OH:25].[OH-].[Na+].Cl>C(O)C>[CH3:1][C:2]1[N:3]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[CH3:22])[C:4]([C:7](=[N:24][OH:25])[CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[N:5][N:6]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 902812771-(5-methyl-4-(o-tolyl)-4H-1,2,4-triazol-3-yl)-2-phenylethanone

Product 1

HCID 1366114361-(5-methyl-4-(o-tolyl)-4H-1,2,4-triazol-3-yl)-2-phenylethanone oxime

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of 10D and hydroxylamine hydrochloride (420 mg, 6 mmol) in ethanol (5 mL), sodium hydroxide (480 mg, 12 mmol) was added. It was refluxed for two hours. The reaction was acidified with 1 N hydrochloride and extracted with ethyl acetate (50 mL twice). The organic layer was dried with Na2SO4, filtered and concentrated. The crude product was purified by flash column) to provide the desired product. MS (m/z) 307 [M+H]+.

Workup

  1. additionwas added
  2. temperatureIt was refluxed for two hours
  3. extractionextracted with ethyl acetate (50 mL twice)
  4. dry with materialThe organic layer was dried with Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product was purified by flash column)

Sources & evidence

ORD record
ord-58ac350ed02c486d9a3b9df3d37b4385
Source dataset
uspto-grants-2015_12
Patent number
US09220710B2

Reaction notes

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