Sodium Iodide → HCID 89586036, compound

HRID 1747792Notes

Reaction equation

HRID 1747792 reaction equation
[I-].[Na+].Cl[Si](C)(C)C.C[O:9][C:10]1[C:11](=[O:26])[CH:12]=[N:13][N:14]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([F:25])([F:24])[F:23])[CH:17]=2)[CH:15]=1>C(#N)C.O>[OH:9][C:10]1[C:11](=[O:26])[CH:12]=[N:13][N:14]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([F:25])([F:23])[F:24])[CH:17]=2)[CH:15]=1

Participants

6

Reactant 3

HCID 5238Sodium IodideHCID 6397ChlorotrimethylsilaneHCID 89586364HCID 89586364, compound

Product 1

HCID 89586036HCID 89586036, compoundYield 180.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent2×

Procedure

To a solution of sodium iodide (0.513 g) in acetonitrile (4 mL) was added chlorotrimethylsilane (0.434 mL) at room temperature. The reaction mixture was stirred at room temperature for 30 min, a solution of 5-methoxy-1-[3-(trifluoromethyl)phenyl]pyridazin-4(1H)-one (0.185 g) in acetonitrile (6 mL) was added at room temperature. The reaction mixture was heated under reflux for 3 hr, cooled to room temperature, diluted with water, extracted with ethyl acetate, washed with saturated brine, dried over anhydrous sodium sulfate, filtered, concentrated, and purified by silica gel column chromatography (ethyl acetate/hexane-methanol/ethyl acetate) to give the title compound (0.317 g).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 3 hr
  3. temperaturecooled to room temperature
  4. extractionextracted with ethyl acetate
  5. washwashed with saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. custompurified by silica gel column chromatography (ethyl acetate/hexane-methanol/ethyl acetate)

Sources & evidence

ORD record
ord-c164be3ef7c54730b4a73b2f21b9cbe7
Source dataset
uspto-grants-2015_10
Patent number
US09150588B2

Reaction notes

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