Ethyl orthoformate → 1-(4-Bromophenyl)-1,2-dihydro-3H-1,2,4-triazol-3-one

HRID 1772611Notes

Reaction equation

HRID 1772611 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][NH:9][C:10]([NH2:12])=[O:11])=[CH:4][CH:3]=1.[CH2:13](OC(OCC)OCC)C>>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH:13]=[N:12][C:10](=[O:11])[NH:9]2)=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 31214Ethyl orthoformateHCID 19692579HCID 19692579, compound

Product 1

HCID 234341921-(4-Bromophenyl)-1,2-dihydro-3H-1,2,4-triazol-3-oneYield 73%

Procedure

A solution of compound 11a (10.0 g, 43.5 mmol) in triethoxymethane (300 mL) was stirred at 120° C. for 2 h. The reaction mixture was cooled in a water/ice bath. The resulting solids were collected by filtration and washed with Et2O to obtain compound 11b as a grey solid (7.80 g, 73% yield). Mass Spectrum (LCMS, ESI pos.): Calcd. for C8H6BrN3O: 240.0 (M+H). Found 240.2.

Workup

  1. temperatureThe reaction mixture was cooled in a water/ice bath
  2. filtrationThe resulting solids were collected by filtration
  3. washwashed with Et2O

Sources & evidence

ORD record
ord-5fe78c9159ea42ffb7d39361fba6a2e0
Source dataset
uspto-grants-2016_02
Patent number
US09249163B2

Reaction notes

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