Triphosgene → 8-Chloro-7-(4-methylphenyl)[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one

HRID 2101276Notes

Reaction equation

HRID 2101276 reaction equation
Cl[C:2](Cl)([O:4]C(=O)OC(Cl)(Cl)Cl)Cl.[Cl:13][C:14]1[C:15]([NH:27][NH2:28])=[N:16][CH:17]=[CH:18][C:19]=1[C:20]1[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][CH:21]=1>C1COCC1>[Cl:13][C:14]1[C:15]2[N:16]([C:2](=[O:4])[NH:28][N:27]=2)[CH:17]=[CH:18][C:19]=1[C:20]1[CH:21]=[CH:22][C:23]([CH3:26])=[CH:24][CH:25]=1

Participants

4

Reactant 2

HCID 94429TriphosgeneHCID 577993761-(3-Chloro-4-p-tolylpyridin-2-yl)hydrazine

Product 1

HCID 577993938-Chloro-7-(4-methylphenyl)[1,2,4]triazolo[4,3-a]pyridin-3(2H)-oneYield 72.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of triphosgene (2.64 g, 8.9 mmol) in THF (25 mL) at room temperature under argon was added 1-(3-chloro-4-p-tolylpyridin-2-yl)hydrazine (0.692 g, 3.0 mmol). The reaction mixture was stirred at room temperature for 16 h. Analysis by HPLC/MS indicated that starting material had been consumed. Water (25 mL) was added while stirring. The resulting suspension was heated at 100° C. for 40 h. Upon cooling to room temperature, the desired product was filtered and further washed with water (15 mL×2). After drying in a vacuum oven under reduced pressure overnight, 562 mg of the title compound was obtained as a white solid. HPLC/MS: retention time=2.98 min, [M+H]+=260.

Workup

  1. customhad been consumed
  2. additionWater (25 mL) was added
  3. stirringwhile stirring
  4. temperatureThe resulting suspension was heated at 100° C. for 40 h
  5. temperatureUpon cooling to room temperature
  6. filtrationthe desired product was filtered
  7. washfurther washed with water (15 mL×2)
  8. customAfter drying in a vacuum oven under reduced pressure overnight

Sources & evidence

ORD record
ord-6e7e5d9d08c2468bac43c4c8b34772f2
Source dataset
uspto-grants-2009_08
Patent number
US07572808B2

Reaction notes

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