Hydrochloric Acid → 3-Chloro-6-iodopyrazine-2-carbonitrile

HRID 334387Notes

Reaction equation

HRID 334387 reaction equation
[ClH:1].N[C:3]1[C:4]([C:10]#[N:11])=[N:5][C:6]([I:9])=[CH:7][N:8]=1.N([O-])=O.[Na+]>O>[Cl:1][C:3]1[C:4]([C:10]#[N:11])=[N:5][C:6]([I:9])=[CH:7][N:8]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 23668193Sodium Nitrite2×HCID 866805543-Amino-6-iodopyrazine-2-carbonitrile

Product 1

HCID 866805553-Chloro-6-iodopyrazine-2-carbonitrileYield 44%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
-50 °C

Procedure

64.3 ml of hydrochloric acid is added at −5° C. to 7.7 g (31.3 mmol) of 3-amino-6-iodopyrazine-2-carbonitrile. At this temperature, a sodium nitrite solution (4.32 g, 62.6 mmol) dissolved in 9 ml of water is added to the reaction mixture and is stirred for 4 hours at −50° C. and then at room temperature overnight. Another equivalent of sodium nitrite is added to the reaction mixture and the precipitate formed is filtered, rinsed with water and dried at 50° C. to yield 3.65 g (44%) of 3-chloro-6-iodopyrazine-2-carbonitrile in the form of a beige solid.

Workup

  1. additionis added to the reaction mixture
  2. customat room temperature
  3. customovernight
  4. customthe precipitate formed
  5. filtrationis filtered
  6. washrinsed with water
  7. customdried at 50° C.

Sources & evidence

ORD record
ord-2b298064153a4b258f08d68c7a516048
Source dataset
uspto-grants-2014_11
Patent number
US08883821B2

Reaction notes

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