Chlorine → N-Chlorophthalimide

HRID 2082701Notes

Reaction equation

HRID 2082701 reaction equation
[Cl:1]Cl.[C:3]1(=[O:13])[NH:7][C:6](=[O:8])[C:5]2=[CH:9][CH:10]=[CH:11][CH:12]=[C:4]12.[K]>C(Cl)Cl>[Cl:1][N:7]1[C:3](=[O:13])[C:4]2=[CH:12][CH:11]=[CH:10][CH:9]=[C:5]2[C:6]1=[O:8]

Participants

4

Reactant 2

HCID 24526Chlorine2×HCID 24194345Phthalimide potassium salt

Product 1

HCID 18997N-Chlorophthalimide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
20 °C

Procedure

Chlorine gas was added to one liter of methylene chloride for 20 minutes at 0° C. during which time saturation was achieved. Potassium phthalimide (50 grams; 270 mmoles) was added to the chlorine-saturated methylene chloride. Cooling was discontinued, and the mixture was stirred for two hours during which time the mixture warmed to 20° C. The resulting slightly greenish-yellow mixture was evaporated to a slush without filtering, and water was added to the mixture to dissolve the resulting potassium chloride. The total mixture was filtered, and the solid which was collected was washed with water and then with heptane. The solid was vacuum-dried overnight to obtain 46.4 grams (95.% yield) of N-chlorophthalimide.

Workup

  1. temperatureCooling
  2. customThe resulting slightly greenish-yellow mixture was evaporated to a slush
  3. filtrationwithout filtering
  4. additionwater was added to the mixture
  5. dissolutionto dissolve the resulting potassium chloride
  6. filtrationThe total mixture was filtered
  7. customthe solid which was collected
  8. washwas washed with water
  9. customThe solid was vacuum-dried overnight

Sources & evidence

ORD record
ord-9a657c9a653e46fc813bfae4e327e66c
Source dataset
uspto-grants-1978_04
Patent number
US04082766

Reaction notes

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