Acetyl chloride → HCID 22416558, compound

HRID 1720929Notes

Reaction equation

HRID 1720929 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:8](=[N:12][CH2:13][CH2:14][O:15][N+:16]([O-:18])=[O:17])[NH:9][C:10]#[N:11])[CH:5]=[N:6][CH:7]=1.[C:19](Cl)(=[O:21])[CH3:20].C(=O)([O-])O.[Na+]>N1C=CC=CC=1>[C:19]([NH:1][C:2]1[CH:3]=[C:4]([C:8](=[N:12][CH2:13][CH2:14][O:15][N+:16]([O-:18])=[O:17])[NH:9][C:10]#[N:11])[CH:5]=[N:6][CH:7]=1)(=[O:21])[CH3:20]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 516892Sodium BicarbonateHCID 22416552HCID 22416552, compound

Product 1

HCID 22416558HCID 22416558, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 5-amino-N-cyano-N'-(2-nitroxyethyl)-3-pyridinecarboximidamide (105 mg, 0.42 mmol) (see Example 1) in pyridine (1 ml) was added acetyl chloride (45 μl, 0.63 mmol), and the mixture was reacted at room temperature for 1 hour. After the reaction was completed, a cold aqueous sodium hydrogen carbonate solution was added, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue thus obtained was purified by silica gel column chromatography with a mixed solvent of methanol and chloroform as an eluent to give the title compound (116 mg, yield 95%) as hygroscopic powder.

Workup

  1. customthe mixture was reacted at room temperature for 1 hour
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue thus obtained
  7. customwas purified by silica gel column chromatography with a mixed solvent of methanol and chloroform as an eluent

Sources & evidence

ORD record
ord-6bd833ed68a44cf29e3d0769ae990429
Source dataset
uspto-grants-1996_04
Patent number
US05508293

Reaction notes

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