Phosphorus oxychloride → 3-[3-(3-Methoxypropyl)-5-(6-phenylpyridin-3-yl)-4H-1,2,4-triazol-4-yl]-2-methylbenzonitrile

HRID 6929Notes

Reaction equation

HRID 6929 reaction equation
P(Cl)(Cl)(Cl)=O.[CH3:6][O:7][CH2:8][CH2:9][CH2:10][C:11]1[N:15]([C:16]2[C:17]([CH3:25])=[C:18]([CH:22]=[CH:23][CH:24]=2)[C:19]([NH2:21])=O)[C:14]([C:26]2[CH:27]=[N:28][C:29]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)=[CH:30][CH:31]=2)=[N:13][N:12]=1>>[CH3:6][O:7][CH2:8][CH2:9][CH2:10][C:11]1[N:15]([C:16]2[C:17]([CH3:25])=[C:18]([CH:22]=[CH:23][CH:24]=2)[C:19]#[N:21])[C:14]([C:26]2[CH:27]=[N:28][C:29]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)=[CH:30][CH:31]=2)=[N:13][N:12]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 220192513-[3-(3-Methoxypropyl)-5-(6-phenylpyridin-3-yl)-1,2,4-triazol-4-yl]-2-methylbenzamide

Product 1

HCID 102015733-[3-(3-Methoxypropyl)-5-(6-phenylpyridin-3-yl)-4H-1,2,4-triazol-4-yl]-2-methylbenzonitrileYield 52.3%

Procedure

Phosphorus oxychloride (8 ml) was added to 3-[3-(3-methoxypropyl)-5-(6-phenylpyridin-3-yl)-1,2,4-triazol-4-yl]-2-methylbenzamide (770 mg) prepared in the Example 4, and refluxed under heating for 3 hours. After the reaction solution was cooled to ambient temperature, the solution was concentrated under reduced pressure. Chloroform was added to the resulting residue, which was then washed with saturated aqueous sodium hydrogen carbonate solution. Subsequently, the organic layer was dried over anhydrous magnesium sulfate. After the solvent was evaporated under reduced pressure, the resulting solid was recrystallized from ethyl acetate, to afford the entitled compound as white crystal (386 mg, 52%). The physico-chemical values are as follows.

Workup

  1. customprepared in the Example 4
  2. temperaturerefluxed
  3. temperatureunder heating for 3 hours
  4. concentrationthe solution was concentrated under reduced pressure
  5. additionChloroform was added to the resulting residue, which
  6. washwas then washed with saturated aqueous sodium hydrogen carbonate solution
  7. dry with materialSubsequently, the organic layer was dried over anhydrous magnesium sulfate
  8. customAfter the solvent was evaporated under reduced pressure
  9. customthe resulting solid was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-72e7e9fd9d714797ab3b1ceb025540aa
Source dataset
uspto-grants-2006_08
Patent number
US07084164B2

Reaction notes

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