Benzoylacetone → HCID 14155100, compound

HRID 1251987Notes

Reaction equation

HRID 1251987 reaction equation
[NH2:1][C:2]1[N:6]=[C:5]([S:7][CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[NH:4][N:3]=1.[C:15]([CH2:23][C:24](=O)[CH3:25])(=O)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C(O)(=O)C>[CH2:8]([S:7][C:5]1[N:6]=[C:2]2[N:1]=[C:15]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH:23]=[C:24]([CH3:25])[N:3]2[N:4]=1)[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 7166BenzoylacetoneHCID 178509291HCID 178509291, compound

Product 1

HCID 14155100HCID 14155100, compoundYield 14.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 20.6 g (100 mmol) of 3-amino-5-benzylthio-1,2,4-triazole and 16.2 g (100 mmol) of benzoyl acetone in 100 ml of glacial acetic acid was heated at reflux for 14 hours. The solvent was removed by evaporation at reduced pressure and the residue was chromatographed on silica gel (HPLC) eluting with EtOAc-hexane (3:7, v/v) to afford 4.81 g (14%) of 2-benzylthio-7-methyl-5-phenyl-1,2,4-triazolo[1,5-a]pyrimidine as a pale yellow wolid, m.p. 154°-155° C. IR and 1H NMR spectra were in agreement with the assigned structure.

Workup

  1. temperatureat reflux for 14 hours
  2. customThe solvent was removed by evaporation at reduced pressure
  3. customthe residue was chromatographed on silica gel (HPLC)
  4. washeluting with EtOAc-hexane (3:7

Sources & evidence

ORD record
ord-52c64524e7c9426690c79bbf58ed385c
Source dataset
uspto-grants-1988_05
Patent number
US04741764

Reaction notes

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