Azobisisobutyronitrile → HCID 22256031, compound

HRID 1611747Notes

Reaction equation

HRID 1611747 reaction equation
[CH3:1][C:2]1[CH:17]=[CH:16][CH:15]=[C:14]([CH3:18])[C:3]=1[C:4]([O:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:5].S(Cl)([Cl:22])(=O)=O.CC(N=NC(C#N)(C)C)(C#N)C.C([O-])(O)=O.[Na+]>C(Cl)(Cl)(Cl)Cl>[Cl:22][CH2:1][C:2]1[CH:17]=[CH:16][CH:15]=[C:14]([CH3:18])[C:3]=1[C:4]([O:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:5]

Participants

6

Reactant 4

HCID 6547AzobisisobutyronitrileHCID 24648Sulfuryl chlorideHCID 516892Sodium BicarbonateHCID 22256033HCID 22256033, compound

Product 1

HCID 22256031HCID 22256031, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

12.0 g of benzyl 2,6-dimethylbenzoate are initially charged into 50 ml of carbon tetrachloride admixed at room temperature with 5.4 g of sulfuryl chloride and 40 mg of AIBN. The mixture is stirred at reflux for 4–5 h. Afterwards, it is admixed with 40 ml of saturated NaHCO3 solution. After the phase separation, the organic phase is washed with 50 ml of 10% sodium sulfite solution, and the organic phase is then dried over magnesium sulfate. The product-containing solution is filtered trough silica gel and washed again with 20 ml of carbon tetrachloride. After distilling off the solvent in vacuo, the product obtained is a bright yellow oil. Yield: 8.0 g (73% of theory; 88.4 area %).

Workup

  1. temperatureat reflux for 4–5 h
  2. customAfter the phase separation
  3. washthe organic phase is washed with 50 ml of 10% sodium sulfite solution
  4. dry with materialthe organic phase is then dried over magnesium sulfate
  5. filtrationThe product-containing solution is filtered trough silica gel
  6. washwashed again with 20 ml of carbon tetrachloride
  7. distillationAfter distilling off the solvent in vacuo
  8. customthe product obtained

Sources & evidence

ORD record
ord-a4133ec2e945442d94b3b24fe5aea726
Source dataset
uspto-grants-2006_01
Patent number
US06989462B2

Reaction notes

Loading…