Chlorosuccinimide → HCID 9991307, compound

HRID 1611745Notes

Reaction equation

HRID 1611745 reaction equation
[CH3:1][C:2]1[CH:13]=[CH:12][CH:11]=[C:10]([CH3:14])[C:3]=1[C:4]([O:6][CH:7]([CH3:9])[CH3:8])=[O:5].[Cl:15]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.CC(N=NC(C#N)(C)C)(C#N)C>[Cl:15][CH2:1][C:2]1[CH:13]=[CH:12][CH:11]=[C:10]([CH3:14])[C:3]=1[C:4]([O:6][CH:7]([CH3:9])[CH3:8])=[O:5]

Participants

5

Reactant 2

HCID 31398ChlorosuccinimideHCID 11961890HCID 11961890, compound

Product 1

HCID 9991307HCID 9991307, compoundYield 96.5%

Reagents, catalysts & solvents 2

HCID 6547AzobisisobutyronitrileCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

19.2 g of isopropyl 2,6-dimethylbenzoate are initially charged in 100 ml of carbon tetrachloride admixed at room temperature with 13.3 g of N-chlorosuccinimide and 200 mg of AIBN. The mixture is heated to reflux for 3 h. After the mixture has been cooled, it is filtered with suction, and the succinimide is washed with 20 ml of carbon tetrachloride. The filtrates are combined, and carbon tetrachloride is distilled off in vacuo. 21.8 g of colorless liquid are obtained. The product is distilled under high vacuum (0.05 mbar, 94–97° C.). Yield: 13.9 g (61% of theory; 93.6 area %).

Workup

  1. temperatureThe mixture is heated
  2. temperatureto reflux for 3 h
  3. temperatureAfter the mixture has been cooled
  4. filtrationit is filtered with suction
  5. washthe succinimide is washed with 20 ml of carbon tetrachloride
  6. distillationcarbon tetrachloride is distilled off in vacuo

Sources & evidence

ORD record
ord-4712b3ad6d8b46d8ad7024a2280d9fa2
Source dataset
uspto-grants-2006_01
Patent number
US06989462B2

Reaction notes

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