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

HRID 1487357Notes

Reaction equation

HRID 1487357 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-f93cbc89c4664bffb5fa957a5b8f1248
Source dataset
uspto-grants-2016_08
Patent number
US09428510B2

Reaction notes

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