Acetic Anhydride → N-(6-chloropyrazin-2-yl)acetamide

HRID 2182173Notes

Reaction equation

HRID 2182173 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([NH2:8])[CH:5]=[N:4][CH:3]=1.[C:9](OC(=O)C)(=[O:11])[CH3:10].C([O-])(O)=O.[Na+]>C(O)(=O)C>[Cl:1][C:2]1[N:7]=[C:6]([NH:8][C:9](=[O:11])[CH3:10])[CH:5]=[N:4][CH:3]=1

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 1184582-Amino-6-ChloropyrazineHCID 516892Sodium Bicarbonate

Product 1

HCID 14787673N-(6-chloropyrazin-2-yl)acetamide

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 6-chloro-pyrazin-2-ylamine (50 mg, 0.38 mmol) in acetic acid (1.9 mL) was treated with acetic anhydride (0.04 mL, 0.42 mmol). The mixture was heated to reflux for 1 h, cooled to room temperature, then poured into saturated NaHCO3 (30 mL) and extracted with ethyl acetate (2×30 mL). The organic layers were combined, washed with brine, dried (Na2SO4), filtered, and concentrated to dryness to give the title compound I-5a (58.6 mg).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 1 h
  3. extractionextracted with ethyl acetate (2×30 mL)
  4. washwashed with brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-269b869f5c274f788c98040321e17fb1
Source dataset
uspto-grants-2005_05
Patent number
US06894050B2

Reaction notes

Loading…