Propylene Oxide → N-Chlorophthalimide

HRID 46728

Reaction equation

HRID 46728 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.C1OC1C.N1C2C(=CC=CC=2)C=CC=1.[Cl:26]Cl>C(Cl)Cl>[Cl:26][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 4

HCID 6378Propylene OxideHCID 6809Phthalimide2×HCID 7047QuinolineHCID 24526Chlorine

Product 1

HCID 18997N-Chlorophthalimide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To 150 ml. of methylene chloride were added 7.35 g. (0.05 mole) of phthalimide and 17.5 ml. (5 equiv.) of propylene oxide. The resulting mixture was cooled to 0° C., 0.13 g. (0.001 mole; 0.02 equiv.) of quinoline was added, and the mixture was saturated with chlorine. The phthalimide began to dissolve within 30 minutes, and after one hour it was nearly all dissolved. Analysis of the sample by TLC at 1.25 hours showed only a trace of starting material. The mixture was subjected to partial vacuum to remove excess chlorine, and a small amount of amylene was added. The resulting mixture then was evaporated to obtain crystalline N-chlorophthalimide. The product was filtered and vacuum dried overnight to give 8.2 g. (90.4%) of product. Analysis: (1) Percent Cl+ : Theory: 19.6; Found: 19.3. (2) Percent total chlorine: 19.1.

Workup

  1. dissolutionto dissolve within 30 minutes
  2. waitAnalysis of the sample by TLC at 1.25 hours showed only
  3. customto remove excess chlorine
  4. additiona small amount of amylene was added
  5. customThe resulting mixture then was evaporated

Sources & evidence

ORD record
ord-2f26cd228afd474bb813427d4b38d35d
Source dataset
uspto-grants-1979_11
Patent number
US04175082

Linked notes

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