Thionyl Chloride → HCID 19701330, compound

HRID 861987Notes

Reaction equation

HRID 861987 reaction equation
O[CH2:2][C:3]1[C:4]2[N:5]([CH:9]=[C:10]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[N:11]=2)[CH:6]=[CH:7][CH:8]=1.S(Cl)([Cl:19])=O>C(Cl)(Cl)Cl>[Cl:19][CH2:2][C:3]1[C:4]2[N:5]([CH:9]=[C:10]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[N:11]=2)[CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 19701226HCID 19701226, compound

Product 1

HCID 19701330HCID 19701330, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

The product from Example 20 (5.0 g, 23 mmol) was dissolved in CHCl3 (50 mL) and placed in a 100 mL flask. Thionylchloride (2.97 g, 25 mmol) was added dropwise to the reaction. The reaction was heated to reflux for 1 h. After cooling the reaction to room temperature, aq KHCO3 was added to the solution, and product was extracted with CHCl3. The organic extracts were dried (MgSO4), treated with activated charcoal, filtered and stripped in vacuo to leave the title compound as a tan solid (4.97 g, 91%).

Workup

  1. customplaced in a 100 mL flask
  2. temperatureThe reaction was heated
  3. temperatureto reflux for 1 h
  4. temperatureAfter cooling
  5. customthe reaction to room temperature
  6. extractionwas extracted with CHCl3
  7. dry with materialThe organic extracts were dried (MgSO4)
  8. additiontreated with activated charcoal
  9. filtrationfiltered

Sources & evidence

ORD record
ord-3a54d1f6578d4365974de20252ec40e2
Source dataset
uspto-grants-1998_02
Patent number
US05716964

Reaction notes

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