Hydrochloric Acid → N-(7-chloro-6-oxooctyl)phthalimide

HRID 224982

Reaction equation

HRID 224982 reaction equation
[C:1]1(=[O:19])[N:5]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11](Cl)=[O:12])[C:4](=[O:14])[C:3]2=[CH:15][CH:16]=[CH:17][CH:18]=[C:2]12.[N+](=[CH:22][CH3:23])=[N-].[ClH:24]>C1(C)C=CC=CC=1.CC(C)=O>[Cl:24][CH:22]([CH3:23])[C:11](=[O:12])[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][N:5]1[C:4](=[O:14])[C:3]2=[CH:15][CH:16]=[CH:17][CH:18]=[C:2]2[C:1]1=[O:19]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 70695DiazoethaneHCID 594868N-(6-Chloro-6-oxohexyl)phthalimide

Product 1

HCID 23330871N-(7-chloro-6-oxooctyl)phthalimide

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 1140TolueneSolvent

Procedure

A solution of 6-phthalimidohexanoyl chloride (2 g.) in dry toluene was added to an ethereal solution of diazoethane at -78° C. and the mixture was allowed to warm to room temperature and stand for 15 hours. On standing a solid crystallized out of solution. The reaction mixture was filtered and the filtrate evaporated to dryness giving 1.43 g. of yellow-green oil. This oil was then dissolved in acetone and concentrated hydrochloric acid added until effervescence ceased. The resulting yellow-brown solution was then evaporated to dryness and azeotroped three times with toluene to give N-(7-chloro-6-oxooctyl)phthalimide (1.4 g.) which was used without further purification.

Workup

  1. customcrystallized out of solution
  2. filtrationThe reaction mixture was filtered
  3. customthe filtrate evaporated to dryness
  4. customgiving 1.43 g
  5. customThe resulting yellow-brown solution was then evaporated to dryness
  6. customazeotroped three times with toluene

Sources & evidence

ORD record
ord-a5b1bb4e06e34b869b0d0326ce8b2fd5
Source dataset
uspto-grants-1980_11
Patent number
US04234735

Linked notes

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