Chloroform → HCID 22247880, compound

HRID 392350Notes

Reaction equation

HRID 392350 reaction equation
N[C:2]1[N:7]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[C:5]([O:12][CH3:13])=[N:4][CH:3]=1.N([O-])=O.[Na+].C(Cl)(Cl)Cl.C(=O)([O-])O.[Na+].[FH:27]>N1C=CC=CC=1>[F:27][C:2]1[N:7]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[C:5]([O:12][CH3:13])=[N:4][CH:3]=1

Participants

7

Reactant 5

HCID 6212ChloroformHCID 14917Hydrofluoric AcidHCID 516892Sodium BicarbonateHCID 22662843Methyl 6-amino-3-methoxy-2-pyrazinecarboxylateHCID 23668193Sodium Nitrite

Product 1

HCID 22247880HCID 22247880, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

In 140 mL of 70% solution of hydrogen fluoride in pyridine was dissolved 17.3 g of methyl 6-amino-3-methoxy-2-pyrazinecarboxylate at an ice-cooled temperature. Then, 7.8 g of sodium nitrite was added at −50° C. in three portions. After the foaming had ceased, the temperature was slowly elevated, and the mixture was stirred at room temperature for 30 minutes. The reaction mixture was poured into a mixture of 300 mL of ice and 200 mL of chloroform, the deposited insoluble matter was filtered off, and then the organic layer was separated. The remaining aqueous layer was extracted with ten portions of chloroform, provided that the total quantity of liquid came to 500 mL. The organic layers thus obtained were united, pH was adjusted to 7 with a saturated aqueous solution of sodium hydrogen carbonate, and the organic layer was separated. The organic layer thus obtained was washed with saturated aqueous solution of sodium chloride and dried on anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue thus obtained was purified by silica gel chromatography [eluent: n-hexane:ethyl acetate=4:1] to obtain 14.3 g of methyl 6-fluoro-3-methoxy-2-pyrazinecarboxylate as a solid product.

Workup

  1. temperaturecooled temperature
  2. filtrationthe deposited insoluble matter was filtered off
  3. customthe organic layer was separated
  4. extractionThe remaining aqueous layer was extracted with ten portions of chloroform
  5. customprovided that the total quantity of liquid
  6. customThe organic layers thus obtained
  7. customthe organic layer was separated
  8. customThe organic layer thus obtained
  9. washwas washed with saturated aqueous solution of sodium chloride
  10. dry with materialdried on anhydrous magnesium sulfate
  11. customthe solvent was removed under reduced pressure
  12. customThe residue thus obtained
  13. customwas purified by silica gel chromatography [eluent: n-hexane:ethyl acetate=4:1]

Sources & evidence

ORD record
ord-c73d3d3497cc4a65a20f2d5ca77cabcf
Source dataset
uspto-grants-2004_10
Patent number
US06800629B2

Reaction notes

Loading…