Dimethyl Sulfoxide → HCID 68827797, compound

HRID 1987077Notes

Reaction equation

HRID 1987077 reaction equation
Cl[C:2]1[N:7]=[N:6][C:5]([C:8]#[N:9])=[CH:4][CH:3]=1.[N-:10]=[N+:11]=[N-:12].[Na+].CS(C)=O>O>[N:10]1[N:11]=[N:12][N:7]2[C:2]=1[CH:3]=[CH:4][C:5]([C:8]#[N:9])=[N:6]2

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 33557Sodium AzideHCID 133828716-Chloropyridazine-3-carbonitrile

Product 1

HCID 68827797HCID 68827797, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 6-chloropyridazine-3-carbonitrile (291 mg, 2.12 mmol) (Szilagyi, G., et al; European J. Med. Chem. 19:111-117, 1984), sodium azide (149 mg, 2.29 mmol), and DMSO (0.9 mL) was stirred at rt for 20 min, then diluted with water (10 mL), and extracted with EtOAc (3×10 mL). The organic layers were combined, washed with brine (1×10 mL), dried (Na2SO4), and the clear pink solution was passed through a silica plug (EtOAc eluent). Treatment with decolorizing charcoal, filtration, and concentration with rotary evaporation afforded the title compound as an off-white solid (243 mg, 1.69 mmol, 80% yield). 1H-NMR (300 MHz, CDCl3) δ 8.66 (d, J=9.3 Hz, 1H), 7.81 (d, J=9.3 Hz, 1H).

Workup

  1. extractionextracted with EtOAc (3×10 mL)
  2. washwashed with brine (1×10 mL)
  3. dry with materialdried (Na2SO4)
  4. filtrationTreatment with decolorizing charcoal, filtration, and concentration
  5. customwith rotary evaporation

Sources & evidence

ORD record
ord-80991d7c5abc450ab14395f55721b273
Source dataset
uspto-grants-2009_06
Patent number
US07550474B2

Reaction notes

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