p-Toluenesulfonic acid → 3-Methyl-6-phenyl-1,2,4-triazine 4-oxide
Reaction equation
[N:1](=[C:3]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[CH:4]=[N:5][OH:6])[NH2:2].[C:13](OC)(OC)(OC)[CH3:14].C1(C)C=CC(S(O)(=O)=O)=CC=1>ClCCl>[CH3:13][C:14]1[N:2]=[N:1][C:3]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[CH:4][N+:5]=1[O-:6]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 130 °C
Procedure
To a solution of hydrazono-phenyl-acetaldehyde oxime (28 g, 168 mmol) at room temperature under nitrogen in dichloromethane (300 ml) was added trimethyl orthoacetate (19 ml, 168 mmol) and p-toluenesulfonic acid (1.6 g, 8.4 mmol). The reaction mixture was stirred for 18 h and then concentrated in vacuo. Xylene (300 ml) was added followed by trimethyl orthoacetate (19 ml, 168 mmol) and the mixture heated to 130° C. for 2 h. The reaction mixture was evaporated in vacuo. The residue was purified by flash chromatography (SiO2; 50% EtOAc in hexanes) and the product was recrystallised from a mixture of dichloromethane and ethyl acetate to afford the title compound as a white solid (11.5 g). δH (400 MHz; CDCl3) 2.86 (3H, s), 7.57 (3H, m), 7.99 (2H, m), 8.52 (1H, s). m/z (ES+) 188 (M+1).
Workup
- concentrationconcentrated in vacuo
- additionXylene (300 ml) was added
- customThe reaction mixture was evaporated in vacuo
- customThe residue was purified by flash chromatography (SiO2; 50% EtOAc in hexanes)
- customthe product was recrystallised from a mixture of dichloromethane and ethyl acetate
Sources & evidence
- ORD record
- ord-cdd2f4ff992742b78dfcfe8614148996
- Source dataset
- uspto-grants-2003_08
- Patent number
- US06608062B1
Reaction notes
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