1H-1,2,4-Triazole → HCID 53837266, compound

HRID 1703439Notes

Reaction equation

HRID 1703439 reaction equation
[NH:1]1[CH:5]=[N:4][CH:3]=[N:2]1.Br[CH:7]([N:14]1[C:18](=[O:19])[C:17]2=[CH:20][CH:21]=[CH:22][CH:23]=[C:16]2[C:15]1=[O:24])[C:8](=[O:13])[C:9]([CH3:12])([CH3:11])[CH3:10]>>[CH3:10][C:9]([CH3:12])([CH3:11])[C:8](=[O:13])[CH:7]([N:14]1[C:18](=[O:19])[C:17]2=[CH:20][CH:21]=[CH:22][CH:23]=[C:16]2[C:15]1=[O:24])[N:4]1[CH:3]=[N:2][N:1]=[CH:5]1

Participants

3

Reactant 2

HCID 92571H-1,2,4-TriazoleHCID 22761231HCID 22761231, compound

Product 1

HCID 53837266HCID 53837266, compoundYield 23.4%

Procedure

21 g (0.3 mol) of 1,2,4-triazole were added to 32.4 g (0.1 mol) of 1-bromo-3,3-dimethyl-1-phthalimido-butan-2-one in 200 ml of acetontrile. The mixture was heated for 24 hours under reflux and was then concentrated in a waterpump vacuum. The residue was taken up in 200 ml of methylene chloride and the solution was washed three times in 100 ml of water at a time, dried over sodium sulphate and concentrated in vacuo by distilling off the solvent. The residue was taken up in 200 ml of acetone, the solution was heated with active charcoal and filtered, and 18 g of 1,5-naphthalenedisulphonic acid were added to the filtrate. The resulting precipitate (25.4 g of the naphthalenedisulphonate salt of melting point 155°-162° C., with decomposition) was neutralized with sodium hydrogen carbonate solution. The oil thereby formed was recrystallized from petroleum ether/ethanol. 7.3 g (23% of theory) of 3,3-dimethyl-1-phthalimido-1-(1,2,4-triazol-4-yl)-butan-2 -one of melting point 189°-196° C. were obtained.

Workup

  1. temperatureThe mixture was heated for 24 hours
  2. temperatureunder reflux
  3. concentrationwas then concentrated in a waterpump vacuum
  4. washthe solution was washed three times in 100 ml of water at a time
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated in vacuo
  7. distillationby distilling off the solvent
  8. temperaturethe solution was heated with active charcoal
  9. filtrationfiltered
  10. addition18 g of 1,5-naphthalenedisulphonic acid were added to the filtrate
  11. customThe oil thereby formed
  12. customwas recrystallized from petroleum ether/ethanol

Sources & evidence

ORD record
ord-9e9bf4e5a088438a92f20018382bc4ec
Source dataset
uspto-grants-1978_11
Patent number
US04124369

Reaction notes

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