Propanedioic acid, (1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-, diethyl ester → HCID 10875852, compound

HRID 581392Notes

Reaction equation

HRID 581392 reaction equation
[C:1]1(=[O:22])[N:5]([CH:6]([C:12]([O:14]CC)=O)[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.[Cl:23][C:24]1[CH:30]=[C:29]([S:31]([CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH3:45])(=[O:33])=[O:32])[CH:28]=[CH:27][C:25]=1[NH2:26]>C1(C)C(C)=CC=CC=1>[Cl:23][C:24]1[CH:30]=[C:29]([S:31]([CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH3:45])(=[O:32])=[O:33])[CH:28]=[CH:27][C:25]=1[NH:26][C:12](=[O:14])[CH:6]([N:5]1[C:4](=[O:17])[C:3]2=[CH:18][CH:19]=[CH:20][CH:21]=[C:2]2[C:1]1=[O:22])[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 108613032-Chloro-4-dodecylsulfonylaniline

Product 1

HCID 10875852HCID 10875852, compound

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

Diethyl 2-phthalimidomalonate (obtained from Aldrich Chemical Company Limited) (9.8 g, 32.0 mmol) and 2-chloro-4-dodecylsulphonylaniline (11.5 g, 32.0 mmol) were added to xylene (250 ml) and refluxed under a Dean and Stark trap for 96 hr. The distillate was periodically removed and the main bulk of solvent replenished as necessary. Removal of the xylene solvent under reduced pressure afforded a light brown oil which was purified by column chromatography using a 4:1 mixture of 60-80° C. petroleum ether:ethyl acetate and silica gel. The product, coupler (C13), was obtained as a white solid which was slurried with a little petroleum ether, filtered and dried in air, 13.6 g, 67%.

Workup

  1. temperaturerefluxed under a Dean and Stark trap for 96 hr
  2. customThe distillate was periodically removed
  3. customRemoval of the xylene solvent under reduced pressure
  4. customafforded a light brown oil which
  5. customwas purified by column chromatography
  6. additiona 4:1 mixture of 60-80° C. petroleum ether
  7. customThe product, coupler (C13), was obtained as a white solid which
  8. filtrationfiltered
  9. customdried in air, 13.6 g, 67%

Sources & evidence

ORD record
ord-fac4538d97994630a882626d791dd64f
Source dataset
uspto-grants-1999_07
Patent number
US05919969

Reaction notes

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