Chlorine → N-Chlorophthalimide

HRID 2082698Notes

Reaction equation

HRID 2082698 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]>>[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

3

Reactant 2

HCID 24526Chlorine2×HCID 24194345Phthalimide potassium salt

Product 1

HCID 18997N-ChlorophthalimideYield 91%

Conditions

Temperature
0 °C

Procedure

Chlorine gas was bubbled into one liter of methylene chloride maintained at 0° C. The chlorine was added for about 10 minutes and until saturation was achieved. To the resulting chlorine-saturated methylene chloride were added 50 grams (270 mmoles) of potassium phthalimide as a solid and in one portion. The resulting mixture was allowed to warm gradually to 20° C., and additional chlorine was introduced as a gas during two separate periods to ensure the presence of an excess of chlorine. The mixture then was stirred vigorously at 20° C. for 60-90 minutes. The resulting precipitated potassium chloride was removed by filtration, and the filtrate was evaporated in vacuo to dryness. The residual white solid was suspended in 150 ml. of water for a few minutes, filtered, and washed with 100 ml. of water. The solid was vacuum dried overnight to obtain 44.5 grams (91% yield) of N-chlorophthalimide.

Workup

  1. customChlorine gas was bubbled into one liter of methylene chloride
  2. additionThe chlorine was added for about 10 minutes and until saturation
  3. temperatureto warm gradually to 20° C.
  4. customseparate periods
  5. customThe resulting precipitated potassium chloride
  6. customwas removed by filtration
  7. customthe filtrate was evaporated in vacuo to dryness
  8. waitof water for a few minutes
  9. filtrationfiltered
  10. washwashed with 100 ml
  11. customdried overnight

Sources & evidence

ORD record
ord-aeb8fa29f76b4be6ab6edda847ffcf17
Source dataset
uspto-grants-1978_04
Patent number
US04082766

Reaction notes

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