Chloroacetonitrile → [(Imidazo[1,5-a]pyridin-3-yl)sulfanyl]acetonitrile

HRID 904745Notes

Reaction equation

HRID 904745 reaction equation
[CH:1]1[NH:2][C:3](=[S:10])[N:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=12.Cl[CH2:12][C:13]#[N:14].C(N(CC)CC)C>C1(C)C=CC=CC=1>[CH:1]1[N:2]=[C:3]([S:10][CH2:12][C:13]#[N:14])[N:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=12

Participants

5

Reactant 3

HCID 7856ChloroacetonitrileHCID 8471TriethylamineHCID 73731276259-00-2

Product 1

HCID 13255457[(Imidazo[1,5-a]pyridin-3-yl)sulfanyl]acetonitrile

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

51.0 g (0.315 m) imidazo[1,5-a]pyridine-3(2H)-thione, prepared according to Example 1, 27.6 g (0.365 m) chloroacetonitrile and 30.7 g triethylamine are dissolved in 600 ml of toluene and the solution is heated to reflux for 3 hr, then allowed to cool to room temperature. The toluene solution is washed with water, dried over anhydrous magnesium sulfate and treated with Darco. After the solvent is removed, the residual solid is recrystallized from cyclohexane. A total yield of 62 g is obtained. The recrystallized sample has a melting point of 120°-2° C.

Workup

  1. temperaturethe solution is heated
  2. temperatureto reflux for 3 hr
  3. washThe toluene solution is washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. additiontreated with Darco
  6. customAfter the solvent is removed
  7. customthe residual solid is recrystallized from cyclohexane
  8. customA total yield of 62 g is obtained

Sources & evidence

ORD record
ord-268a833190ba4dd693c105f32c50e800
Source dataset
uspto-grants-1983_12
Patent number
US04419516

Reaction notes

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