Chloroform → HCID 22674952, compound

HRID 2063150Notes

Reaction equation

HRID 2063150 reaction equation
N[C:2]1[N:3]=[C:4]([O:11][CH3:12])[C:5]([C:8]([NH2:10])=[O:9])=[N:6][CH:7]=1.N([O-])=O.[Na+].C(Cl)(Cl)Cl.[FH:21].N1C=CC=CC=1>>[F:21][C:2]1[N:3]=[C:4]([O:11][CH3:12])[C:5]([C:8]([NH2:10])=[O:9])=[N:6][CH:7]=1

Participants

5

Reactant 4

HCID 6212ChloroformHCID 64774Pyridine, hydrofluoride (1:1)HCID 22674954HCID 22674954, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 22674952HCID 22674952, compound

Conditions

Temperature
-10 °C

Procedure

In a nitrogen atmosphere, 0.5 g of 5-amino-3-methoxy-2-pyrazinecarboxamide is dissolved in 9 mL of 70% pyridine hydrofluoride under ice-cooling. Then, 0.23 g of sodium nitrite is added thereto at −70° C., and the resulting solution is heated to a temperature of −10° C. in 30 minutes. Further, the solution is stirred at ambient temperature for 30 minutes. A mixture of 30 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 dried over anhydrous magnesium sulfate. The solvent is distilled off under reduced pressure. The residue thus obtained is purified by column chromatography (eluent: chloroform:methanol =10:1) to obtain 0.37 q of 5-fluoro-3-methoxy-2-pyrazinecarboxamide.

Workup

  1. temperaturecooling
  2. additionis added
  3. customthe resulting mixture is separated into layers
  4. washThe organic layer is washed with saturated aqueous solution of sodium chloride
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationThe solvent is distilled off under reduced pressure
  7. customThe residue thus obtained
  8. customis purified by column chromatography (eluent: chloroform:methanol =10:1)

Sources & evidence

ORD record
ord-07a6b6ed530b4b4ab76a7f2d94bfd7dc
Source dataset
uspto-grants-2012_10
Patent number
USRE043748E1

Reaction notes

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