Chloroform → HCID 22662826, compound

HRID 2063148Notes

Reaction equation

HRID 2063148 reaction equation
N[C:2]1[N:7]=[C:6]([C:8]([NH2:10])=[O:9])[C:5]([O:11][CH3:12])=[N:4][CH:3]=1.N([O-])=O.[Na+].C(Cl)(Cl)Cl.[FH:21].N1C=CC=CC=1>>[F:21][C:2]1[N:7]=[C:6]([C:8]([NH2:10])=[O:9])[C:5]([O:11][CH3:12])=[N:4][CH:3]=1

Participants

5

Reactant 4

HCID 6212ChloroformHCID 64774Pyridine, hydrofluoride (1:1)HCID 226628026-Amino-3-methoxy-2-pyrazinecarboxamideHCID 23668193Sodium Nitrite

Product 1

HCID 22662826HCID 22662826, compound

Conditions

Temperature
10 °C

Procedure

In a nitrogen atmosphere, 1.50 g of 6-amino-3-methoxy-2-pyrazinecarboxamide is dissolved in 12 mL of 70% pyridine hydrofluoride under ice-cooling. Then, 0.71 g of sodium nitrite is added thereto at −50° C., and the resulting solution is stirred at 10° C. for 1 hour. The resulting reaction mixture is stirred at ambient temperature for an additional 1 hour. Thereafter, a mixture of 50 mL of ice water and 100 mL of chloroform is added thereto and the resulting mixture is separated into layers. The organic layer is washed with saturated aqueous solution of sodium chloride and saturated aqueous solution of sodium hydrogen carbonate, and dried over anhydrous magnesium sulfate. Then, the solvent is distilled off under reduced pressure to obtain 1.29 g of 6-fluoro-3-methoxy-2-pyrazinecarboxamide.

Workup

  1. temperaturecooling
  2. customThe resulting reaction mixture
  3. stirringis stirred at ambient temperature for an additional 1 hour
  4. additionis added
  5. customthe resulting mixture is separated into layers
  6. washThe organic layer is washed with saturated aqueous solution of sodium chloride and saturated aqueous solution of sodium hydrogen carbonate
  7. dry with materialdried over anhydrous magnesium sulfate
  8. distillationThen, the solvent is distilled off under reduced pressure

Sources & evidence

ORD record
ord-1d7ad0b59ca34c009af7657a47af0f9f
Source dataset
uspto-grants-2012_10
Patent number
USRE043748E1

Reaction notes

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