Ethyl orthoformate → 6-Phenyl-1,2,4-triazine 4-oxide

HRID 396148Notes

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].[CH:13](OCC)(OCC)OCC.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>>[C:7]1([C:3]2[N:1]=[N:2][CH:13]=[N+:5]([O-:6])[CH:4]=2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

Reactant 3

HCID 31214Ethyl orthoformate

HCID 521998p-Toluenesulfonic acid monohydrate

HCID 136388354HCID 136388354, compound

Product 1

HCID 64049796-Phenyl-1,2,4-triazine 4-oxideYield 85%

Conditions

Temperature: 110 °C

Procedure

To a mixture of hydrazono-phenyl-acetaldehyde oxime (30 g, 184 mmol) and triethyl orthoformate (30.6 ml, 184 mmol) was added 4-toluenesulphonic acid monohydrate (3.5 g, 18.4 mmol). The reaction mixture was heated at 110° C. with stirring for 30 min. The cooled reaction mixture was recrystallised from CH2Cl2/hexane to give 27 g (156 mmol, 85%) of 6-phenyl-[1,2,4]triazine-4-oxide as a pale yellow solid. δH (400 MHz; CDCl3) 7.55-7.63 (3H, m, aromatics), 8.01 (2H, dd, J 8.1 and 1.7, aromatics), 8.52 (1H, d, J 1.7, triazine H5), 9.27 (1H, d, J 1.7, triazine H3); m/z (ES+) 174 (M++H, 100%).

Workup

customThe cooled reaction mixture
customwas recrystallised from CH2Cl2/hexane

Sources & evidence

ORD record: ord-fe782515647e43c99abf517ea60ba38e
Source dataset: uspto-grants-2003_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06608062B1

Reaction notes

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