Phosphorus oxychloride → 2-Chloro-5-iodonicotinonitrile

HRID 1487348Notes

Reaction equation

HRID 1487348 reaction equation
P(Cl)(Cl)([Cl:3])=O.O[C:7]1[N:14]=[CH:13][C:12]([I:15])=[CH:11][C:8]=1[C:9]#[N:10]>S(=O)(=O)(O)O.O>[Cl:3][C:7]1[N:14]=[CH:13][C:12]([I:15])=[CH:11][C:8]=1[C:9]#[N:10]

Participants

5

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178510178HCID 178510178, compound

Product 1

HCID 534010402-Chloro-5-iodonicotinonitrileYield 389.6%

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidCatalystHCID 962WaterSolvent

Conditions

Temperature
110 °C

Procedure

30.7 ml (329 mmol) of phosphorus oxychloride at 0° C. and 6 drops of sulfuric acid are added to 9 g (6.6 mmol) of 2-hydroxy-5-iodonicotinonitrile. The reaction mixture is heated at 110° C. for 5 hours and then at room temperature overnight. The reaction mixture is poured in a beaker containing ice and a little water, and a precipitate is formed. The mixture is allowed to gradually return to room temperature and then is filtered and rinsed with water. The solid is dried to yield 6.8 g (70%) of 2-chloro-5-iodonicotinonitrile.

Workup

  1. customat room temperature
  2. customovernight
  3. additionThe reaction mixture is poured in a beaker
  4. additioncontaining ice
  5. customto gradually return to room temperature
  6. filtrationis filtered
  7. washrinsed with water
  8. customThe solid is dried

Sources & evidence

ORD record
ord-bb27466d385e496d8a8ede4257fa78e5
Source dataset
uspto-grants-2016_08
Patent number
US09428510B2

Reaction notes

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