1H-1,2,4-Triazole → (+/-)-N-[4-[2-methyl-1-(1H-1,2,4-triazol-1-yl)propyl]phenyl]acetamide

HRID 349395Notes

Reaction equation

HRID 349395 reaction equation
CS(O[CH:6]([CH:17]([CH3:19])[CH3:18])[C:7]1[CH:12]=[CH:11][C:10]([NH:13][C:14](=[O:16])[CH3:15])=[CH:9][CH:8]=1)(=O)=O.[NH:20]1[CH:24]=[N:23][CH:22]=[N:21]1.C([O-])([O-])=O.[K+].[K+]>CC#N>[CH3:18][CH:17]([CH3:19])[CH:6]([C:7]1[CH:12]=[CH:11][C:10]([NH:13][C:14](=[O:16])[CH3:15])=[CH:9][CH:8]=1)[N:20]1[CH:24]=[N:23][CH:22]=[N:21]1

Participants

5

Reactant 3

HCID 92571H-1,2,4-TriazoleHCID 11430Potassium CarbonateHCID 11055245(+/-)-4-(Acetylamino)-alpha-(1-methylethyl)benzenemethanol methane sulfonate

Product 1

HCID 9903273(+/-)-N-[4-[2-methyl-1-(1H-1,2,4-triazol-1-yl)propyl]phenyl]acetamideYield 25.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of (±)-4-(acetylamino)-α-(1-methylethyl)benzenemethanol methane sulfonate (ester) (0.1541 mol), 1H-1,2,4-triazole (0.308 mol) and K2CO3 (0.308 mol) in CH3CN (500 ml) was stirred and refluxed for 12 hours. The solvent was evaporated and the residue was taken up in water/CH2Cl2. The organic layer was dried, filtered off and the solvent evaporated. The residue was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH 97/3). The pure fractions were collected and evaporated, yielding 10 g (25%) of (±)-N-[4-[2-methyl-1-(1H-1,2,4-triazol-1-yl)propyl]-phenyl]acetamide (compound 153).

Workup

  1. temperaturerefluxed for 12 hours
  2. customThe solvent was evaporated
  3. customThe organic layer was dried
  4. filtrationfiltered off
  5. customthe solvent evaporated
  6. customThe residue was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH 97/3)
  7. customThe pure fractions were collected
  8. customevaporated

Sources & evidence

ORD record
ord-458376b86d164e9bb578d7413629d52d
Source dataset
uspto-grants-2007_02
Patent number
US07179825B2

Reaction notes

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