Propanedioic acid, (1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-, diethyl ester → HCID 54092708, compound

HRID 581394Notes

Reaction equation

HRID 581394 reaction equation
[C:1]1(=[O:22])[N:5]([CH:6]([C:12](OCC)=[O:13])[C:7]([O:9][CH2:10][CH3:11])=[O:8])[C:4](=[O:17])[C:3]2=[CH:18][CH:19]=[CH:20][CH:21]=[C:2]12.[NH2:23][C:24]1[CH:25]=[C:26]([CH:42]=[CH:43][C:44]=1[Cl:45])[C:27]([O:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41])=[O:28]>C1(C)C=CC=CC=1>[Cl:45][C:44]1[CH:43]=[CH:42][C:26]([C:27]([O:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41])=[O:28])=[CH:25][C:24]=1[NH:23][C:12](=[O:13])[CH:6]([N:5]1[C:1](=[O:22])[C:2]2=[CH:21][CH:20]=[CH:19][CH:18]=[C:3]2[C:4]1=[O:17])[C:7]([O:9][CH2:10][CH3:11])=[O:8]

Participants

4

Reactant 2

HCID 79760Propanedioic acid, (1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-, diethyl esterHCID 11035192Benzoic acid, 3-amino-4-chloro-, dodecyl ester

Product 1

HCID 54092708HCID 54092708, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Diethyl 2-phthalimidomalonate (15.26 g, 50.0 mmol) and n-dodecyl 3-amino-4-chlorobenzoate (16.99 g, 50.0 mmol) were added to toluene (300 ml) and refluxed under Dean and Stark conditions for 5 days, occasionally removing a small amount of distillate and replenishing the solvent as necessary. The reaction was followed by TLC (1:2 ethyl acetate:60-80° C. petroleum ether), the Rf of the product being between that of the two starting materials. The toluene was removed on the rotary evaporator and on standing the viscous oil solidified. Crystallization from 60-80° C. petroleum ether gave a white solid, 13.92 g, 47%

Workup

  1. temperaturerefluxed under Dean and Stark conditions for 5 days
  2. customoccasionally removing a small amount of distillate
  3. customwas followed by TLC (1:2 ethyl acetate:60-80° C. petroleum ether)
  4. customThe toluene was removed on the rotary evaporator
  5. customCrystallization from 60-80° C. petroleum ether
  6. customgave a white solid, 13.92 g, 47%

Sources & evidence

ORD record
ord-f021d0992c50471491f68839f0540cc3
Source dataset
uspto-grants-1999_07
Patent number
US05919969

Reaction notes

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