Thionyl Chloride → HCID 11086324, compound

HRID 726517Notes

Reaction equation

HRID 726517 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[N:14]=[C:13]([CH2:15]O)[CH:12]=[CH:11][CH:10]=2)[CH:5]=[CH:4][N:3]=1.S(Cl)([Cl:19])=O.C(=O)([O-])O.[Na+]>O>[Cl:19][CH2:15][C:13]1[CH:12]=[CH:11][CH:10]=[C:9]([O:8][C:6]2[CH:5]=[CH:4][N:3]=[C:2]([Cl:1])[CH:7]=2)[N:14]=1

Participants

5

Reactant 3

HCID 24386Thionyl Chloride2×HCID 516892Sodium BicarbonateHCID 18974745HCID 18974745, compound

Product 1

HCID 11086324HCID 11086324, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 6-[(2-chloro-4-pyridyl)oxy]-2-pyridinemethanol (10.2 g, 0.043 mol) and thionyl chloride (10 mL) is stirred at room temperature for 90 minutes. Excess thionyl chloride is hydrolyzed by adding water to the reaction mixture until no further reaction is observed. The reaction mixture is then neutralized with saturated sodium hydrogen carbonate solution and extracted with dichloromethane. The organic extracts are combined, dried over anhydrous magnesium sulfate, and concentrated in vacuo to obtain the title product (10.6 g, 97%).

Workup

  1. customuntil no further reaction
  2. extractionextracted with dichloromethane
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-52fb72a78a1744ae98daa1b55b2e2d77
Source dataset
uspto-grants-1998_01
Patent number
US05710106

Reaction notes

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