2-Phenyl-3-sulfanylidene-2,3-dihydro-1H-isoindol-1-one → Phthalimide

HRID 647410Notes

Reaction equation

HRID 647410 reaction equation
ClC1C=CC([N:8]2[CH:16](S)[C:15]3[CH2:14][CH2:13][CH2:12][CH2:11][C:10]=3[C:9]2=[O:18])=C(F)C=1.C1(N2C(=[O:31])C3=CC=CC=C3C2=S)C=CC=CC=1>C1(C)C=CC=CC=1>[C:9]1(=[O:18])[NH:8][C:16](=[O:31])[C:15]2=[CH:14][CH:13]=[CH:12][CH:11]=[C:10]12

Participants

4

Reactant 2

HCID 123508462-Phenyl-3-sulfanylidene-2,3-dihydro-1H-isoindol-1-oneHCID 132575922-(4-chloro-2-fluorophenyl)-2,3,4,5,6,7-hexahydro-3-mercapto-1H-isoindol-1-one

Product 1

HCID 6809Phthalimide

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

In 30 ml of toluene were dissolved 3.0 g of 2-(4-chloro-2-fluorophenyl)-2,3,4,5,6,7-hexahydro-3-mercapto-1H-isoindol 1-one and 2.8 g of N-phenylthio-phthalimide, and the solution was heated under reflux for 3 hours. Upon cooling, there resulted crystals (phthalimide), which were filtered out, and the filtrate was concentrated under reduced pressure. A small amount of toluene was added and, upon standing overnight, there resulted crystals, which were collected by filtration and dried, thereby producing 2.7 g (yield of 67%) of the subject compound. Recrystallization from toluene yielded white crystals m.p. 127°-129° C.

Workup

  1. temperaturethe solution was heated
  2. temperatureunder reflux for 3 hours
  3. temperatureUpon cooling

Sources & evidence

ORD record
ord-c6b75f3ec51d4c229529a1d329d714c8
Source dataset
uspto-grants-1983_10
Patent number
US04409018

Reaction notes

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