Chloroform → HCID 22662826, compound

HRID 392305Notes

Reaction equation

HRID 392305 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.N1C=CC=CC=1.[FH:27]>>[F:27][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 an atmosphere of nitrogen gas, 1.50 g of 6-amino-3-methoxy-2-pyrazinecarboxamide was dissolved in 12 mL of 70% hydrogen fluoride-pyridine solution at an ice-cooled temperature. Then, 0.71 g of sodium nitrite was added at −50° C., and the mixture thus obtained was stirred at 10° C. for one hour. After stirring the reaction mixture for an additional one hour, a mixture of 50 mL of ice water and 100 mL of chloroform was added, and the mixture thus obtained was separated into layers. The organic layer was washed with saturated aqueous solution of sodium chloride and dried on anhydrous magnesium sulfate and the solvent was removed under reduced pressure. Thus, 1.29 g of 6-fluoro-3-methoxy-2-pyrazinecarboxamide was obtained as a solid product.

Workup

  1. temperaturecooled temperature
  2. customthe mixture thus obtained
  3. stirringAfter stirring the reaction mixture for an additional one hour
  4. additionwas added
  5. customthe mixture thus obtained
  6. customwas separated into layers
  7. washThe organic layer was washed with saturated aqueous solution of sodium chloride
  8. dry with materialdried on anhydrous magnesium sulfate
  9. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-0cc52b76adc5400d90a24db69d6b3bd2
Source dataset
uspto-grants-2004_10
Patent number
US06800629B2

Reaction notes

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