p-Chlorothiophenol → 3,4,5-Tris-(p-chlorophenylthio)-6-bromophthalimide

HRID 485970

Reaction equation

HRID 485970 reaction equation
Br[C:2]1[C:3](Br)=[C:4](Br)[C:5]([Br:13])=[C:6]2[C:11](=[O:12])[NH:10][C:8](=[O:9])[C:7]=12.[Cl:16][C:17]1[CH:22]=[CH:21][C:20]([SH:23])=[CH:19][CH:18]=1.C(=O)([O-])[O-].[K+].[K+]>O1CCCC1>[Cl:16][C:17]1[CH:22]=[CH:21][C:20]([S:23][C:2]2[C:3]([S:23][C:20]3[CH:21]=[CH:22][C:17]([Cl:16])=[CH:18][CH:19]=3)=[C:4]([S:23][C:20]3[CH:21]=[CH:22][C:17]([Cl:16])=[CH:18][CH:19]=3)[C:5]([Br:13])=[C:6]3[C:11]([NH:10][C:8](=[O:9])[C:7]=23)=[O:12])=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 7815p-ChlorothiophenolHCID 11430Potassium CarbonateHCID 904903,4,5,6-Tetrabromophthalimide

Product 1

HCID 202695863,4,5-Tris-(p-chlorophenylthio)-6-bromophthalimideYield 25.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2 g (4.46 millimols) of tetrabromophthalimide, 1.61 g (11.15 millimols) of p-chlorothiophenol, 2.31 g (16.73 millimols) of potassium carbonate and 20 ml of tetrahydrofuran are stirred at 25° C. for 14 hours. After acidification with dilute HCl solution, the mixture is extracted with tetrahydrofuran/toluene and the extracts are dried and evaporated. After recrystallisation from toluene/cyclohexane, 0.61 g (25% of theory) of 3,4,5-tris-(p-chlorophenylthio)-6-bromophthalimide is obtained; melting point 164°-9° C.

Workup

  1. extractionAfter acidification with dilute HCl solution, the mixture is extracted with tetrahydrofuran/toluene
  2. customthe extracts are dried
  3. customevaporated
  4. customAfter recrystallisation from toluene/cyclohexane

Sources & evidence

ORD record
ord-37a60ba89cdb4c098ddd35a1a33dd0e4
Source dataset
uspto-grants-1985_08
Patent number
US04537977

Linked notes

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