Acetic Anhydride → HCID 67273906, compound

HRID 1696784Notes

Reaction equation

HRID 1696784 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([C:8]([NH:10][OH:11])=[NH:9])[CH:5]=[C:4]([S:12][CH3:13])[CH:3]=1.[C:14](OC(=O)C)(=O)[CH3:15]>>[CH3:14][C:15]1[O:11][N:10]=[C:8]([C:6]2[N:7]=[C:2]([NH2:1])[CH:3]=[C:4]([S:12][CH3:13])[CH:5]=2)[N:9]=1

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 178503297HCID 178503297, compound

Product 1

HCID 67273906HCID 67273906, compound

Procedure

A solution of 0.094 g 6-Amino-N-hydroxy-4-methylsulfanyl-pyridine-2-carboxamidine in 1.5 ml acetic acid anhydride was heated to reflux for 6 h. The solvent was evaporated and the solidifying residue was taken up in 1.5 ml 1N hydrochloric acid and heated to reflux for 1 h. The reaction mixture was partitioned between 2 ml 1N aqueous sodium hydroxide and ethyl acetate. The phases were separated and the organic phase was washed with water and brine dried over magnesium sulfate and evaporated. The residue triturated in ethyl acetate (1 ml) and the resulting solid was collected by filtration to yield 0.057 g of the title compound as light yellow solid MS (ISP) M+H+=223.3

Workup

  1. temperatureto reflux for 6 h
  2. customThe solvent was evaporated
  3. temperatureheated
  4. temperatureto reflux for 1 h
  5. customThe reaction mixture was partitioned between 2 ml 1N aqueous sodium hydroxide and ethyl acetate
  6. customThe phases were separated
  7. washthe organic phase was washed with water and brine
  8. dry with materialdried over magnesium sulfate
  9. customevaporated
  10. customThe residue triturated in ethyl acetate (1 ml)
  11. filtrationthe resulting solid was collected by filtration

Sources & evidence

ORD record
ord-533634cd030d434998cfbd0ec7613361
Source dataset
uspto-grants-2012_04
Patent number
US08163778B2

Reaction notes

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