Chlorine → N-Chlorophthalimide

HRID 2082700Notes

Reaction equation

HRID 2082700 reaction equation
[C:1]1(=[O:11])[NH:5][C:4](=[O:6])[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12.[K].[Cl:13]Cl>C(Cl)Cl>[Cl:13][N:5]1[C:1](=[O:11])[C:2]2=[CH:10][CH:9]=[CH:8][CH:7]=[C:3]2[C:4]1=[O:6]

Participants

4

Reactant 2

HCID 24526Chlorine2×HCID 24194345Phthalimide potassium salt4×

Product 1

HCID 18997N-ChlorophthalimideYield 88%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent4×

Conditions

Temperature
0 °C

Procedure

To 800 ml. of methylene chloride were added 50 grams (270 mmoles) of potassium phthalimide. The resulting slurry was chilled to 0° C. To a jacketed flask maintained immediately above the main reaction vessel were added 200 ml. of methylene chloride. The methylene chloride was saturated with chlorine and was maintained at a temperature of -5° C. to 0° C. The flask containing the chlorinesaturated methylene chloride was equipped with a dry-ice trap to ensure that none of the reagent escaped. The chlorine-saturated methylene chloride then was added to the potassium phthalimide mixture as rapidly as possible by means of a tube which extended below the surface of the potassium phthalimide slurry. Addition was completed in less than 30 seconds. During addition, the temperature of the mixture increased from 0° C. to 10° C. The resulting mixture had a greenish-yellow color which persisted. The mixture was allowed to warm to 20° C. over a two hour period. Some undissolved lumps of potassium phthalimide were noted in the mixture. The resulting potassium chloride percipitate was removed by filtration, and the filtrate was evaporated in vacuo to a slush. Heptane (about 400 ml.) was added, and the mixture was filtered. The collected N-chlorophthalimide was reslurried in about 500 ml. of water and vacuum-dried to afford 42.9 grams (88% yield) of N-chlorophthalimide.

Workup

  1. temperatureTo a jacketed flask maintained immediately above the main reaction vessel
  2. additionwere added 200 ml
  3. temperaturewas maintained at a temperature of -5° C. to 0° C
  4. customwas equipped with a dry-ice trap
  5. additionAddition
  6. waitwas completed in less than 30 seconds
  7. additionDuring addition
  8. temperaturethe temperature of the mixture increased from 0° C. to 10° C
  9. temperatureto warm to 20° C. over a two hour period
  10. customThe resulting potassium chloride percipitate was removed by filtration
  11. customthe filtrate was evaporated in vacuo to a slush
  12. additionHeptane (about 400 ml.) was added
  13. filtrationthe mixture was filtered
  14. dry with materialof water and vacuum-dried

Sources & evidence

ORD record
ord-e503f98e6e934624a0a8fa92cb547829
Source dataset
uspto-grants-1978_04
Patent number
US04082766

Reaction notes

Loading…