Iodine → Bis-[2-(4-chloro-2-fluorophenyl)-3-oxo-2,3,4,5,6,7-hexahydro-1H-isoindol-1-yl]disulfide

HRID 647411Notes

Reaction equation

HRID 647411 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:16]([SH:17])[C:15]3[CH2:14][CH2:13][CH2:12][CH2:11][C:10]=3[C:9]2=[O:18])=[C:4]([F:19])[CH:3]=1.II>C(O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:9](=[O:18])[C:10]3[CH2:11][CH2:12][CH2:13][CH2:14][C:15]=3[CH:16]2[S:17][S:17][CH:16]2[C:15]3[CH2:14][CH2:13][CH2:12][CH2:11][C:10]=3[C:9](=[O:18])[N:8]2[C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][C:4]=2[F:19])=[C:4]([F:19])[CH:3]=1

Participants

4

Reactant 2

HCID 807IodineHCID 132575922-(4-chloro-2-fluorophenyl)-2,3,4,5,6,7-hexahydro-3-mercapto-1H-isoindol-1-one

Product 1

HCID 13252415Bis-[2-(4-chloro-2-fluorophenyl)-3-oxo-2,3,4,5,6,7-hexahydro-1H-isoindol-1-yl]disulfideYield 57%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In 20 ml of ethanol was dissolved 3.0 g of 2-(4-chloro-2-fluorophenyl)-2,3,4,5,6,7-hexahydro-3-mercapto-1H-isoindol-1-one and 1.4 g of iodine was added to the solution, followed by stirring at room temperature for 5 hours. Upon cooling, there resulted crystals, which were recovered by filtration, washed with ethanol and dried, thereby producing 1.7 g (yield of 57%) of the subject compound. Recrystallization from acetone yielded white crystals, m.p. 146°-147° C.

Workup

  1. additionwas added to the solution
  2. temperatureUpon cooling
  3. customthere resulted crystals, which
  4. filtrationwere recovered by filtration
  5. washwashed with ethanol
  6. customdried

Sources & evidence

ORD record
ord-c406ffa6155f49f5b99ecaad2eddef9e
Source dataset
uspto-grants-1983_10
Patent number
US04409018

Reaction notes

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