Phthalimide → N-Chlorophthalimide

HRID 46727

Reaction equation

HRID 46727 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.O1C(CC)C1.[Cl:17]Cl>CN(C)C1C=CN=CC=1.C(Cl)Cl>[Cl:17][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

6

Reactant 3

HCID 6809PhthalimideHCID 78341,2-EpoxybutaneHCID 24526Chlorine

Product 1

HCID 18997N-Chlorophthalimide

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To 150 ml. of methylene chloride were added 7.35 g. (0.05 mole) of phthalimide, 21.5 ml. (5 equiv.) of 1,2-epoxybutane, and 0.061 g. (0.5 mmoles) of 4-dimethylaminopyridine. The mixture was cooled to 0° C. and saturated with chlorine. The resulting mixture was stirred for 20 hours at room temperature. A sample of the reaction mixture, analyzed by thin-layer chromatography (TLC), indicated that the reaction was not yet complete. The mixture was allowed to stir for an additional 24 hours, and the resulting clear yellow solution was evaporated to obtain crystalline N-chlorophthalimide. The product was vacuum dried to afford 7.7 g. (84.8%) of product. Analysis: (1) Percent Cl+ : Theory: 19.6; Found: 18.3. (2) Percent total chlorine: 18.1.

Workup

  1. stirringto stir for an additional 24 hours
  2. customthe resulting clear yellow solution was evaporated

Sources & evidence

ORD record
ord-0dd2bcc5c80f4544942bbdab9f84b018
Source dataset
uspto-grants-1979_11
Patent number
US04175082

Linked notes

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