Acetyl chloride → HCID 68955615, compound

HRID 1455635Notes

Reaction equation

HRID 1455635 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:8](=[N:10][OH:11])[NH2:9])[CH:5]=[N:6][CH:7]=1.[C:12](Cl)(=O)[CH3:13]>N1C=CC=CC=1.CCOC(C)=O.C([O-])(O)=O.[Na+]>[Br:1][C:2]1[CH:7]=[N:6][CH:5]=[C:4]([C:8]2[N:9]=[C:12]([CH3:13])[O:11][N:10]=2)[CH:3]=1

Participants

6

Reactant 2

HCID 6367Acetyl chloride2×HCID 73739646453565-56-5

Product 1

HCID 68955615HCID 68955615, compound

Reagents, catalysts & solvents 3

HCID 1049PyridineSolventHCID 8857Ethyl AcetateSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 5-bromo-N′-hydroxypyridine-3-carboximidamide (1.0 eq.) in pyridine was added acetyl chloride (2 eq). The reaction stirred at 100° C. for 1 h and 2 eq of acetyl chloride was added. After 1 h, the mixture was cooled, diluted with EtOAc and aqueous NaHCO3. The organic extracts were washed with aqueous NaHCO3, brine, dried over Na2SO4, filtered and concentrated. Flash chromatography (Hex:EtOAc; 70:30) afforded the title compound as a white solid.

Workup

  1. waitAfter 1 h
  2. temperaturethe mixture was cooled
  3. washThe organic extracts were washed with aqueous NaHCO3, brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-34748353cc7147f18bf80fe0931b3dd7
Source dataset
uspto-grants-2009_01
Patent number
US07482456B2

Reaction notes

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