Diacetoxyiodosobenzene → 6-Oxo-1,6-dihydro-[1,2,4]triazine-5-carboxylic acid ethyl ester

HRID 2076828Notes

Reaction equation

HRID 2076828 reaction equation
[CH2:1]([O:3][C:4]([CH:6]1[C:11](=[O:12])[NH:10][N:9]=[CH:8][NH:7]1)=[O:5])[CH3:2].C(OC1C(OC(=O)C)=C(I=O)C=CC=1)(=O)C>C(O)C>[CH2:1]([O:3][C:4]([C:6]1[C:11](=[O:12])[NH:10][N:9]=[CH:8][N:7]=1)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 21113495DiacetoxyiodosobenzeneHCID 178470304HCID 178470304, compound

Product 1

HCID 117152386-Oxo-1,6-dihydro-[1,2,4]triazine-5-carboxylic acid ethyl esterYield 64.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

6-Oxo-1,4,5,6-tetrahydro-[1,2,4]triazine-5-carboxylic acid ethyl ester (329 mg, 1.92 mmol) was dissolved in ethanol (9 ml) and diacetoxyiodosobenzene (644 mg, 1.99 mmol) was added in one portion. After 2 h at ambient temperature all volatiles were removed and the remaining residue was purified by column chromatography (silica gel, heptane/ethyl acetate 70:30 to 50:50) to give the title compound (209 mg, 1.24 mmol; 64%) as yellow solid. MS: m/e=170.1 [M+H+].

Workup

  1. customAfter 2 h at ambient temperature all volatiles were removed
  2. customthe remaining residue was purified by column chromatography (silica gel, heptane/ethyl acetate 70:30 to 50:50)

Sources & evidence

ORD record
ord-8ad4d04b8400455e8a23b1a75102ad92
Source dataset
uspto-grants-2011_04
Patent number
US07928106B2

Reaction notes

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