Potassium Carbonate → Tetrakis-(p-nitrophenylthio)-phthalimide

HRID 1462267Notes

Reaction equation

HRID 1462267 reaction equation
Cl[C:2]1[C:3](Cl)=[C:4](Cl)[C:5](Cl)=[C:6]2[C:11](=[O:12])[NH:10][C:8](=[O:9])[C:7]=12.[N+:16]([C:19]1[CH:24]=[CH:23][C:22]([SH:25])=[CH:21][CH:20]=1)([O-:18])=[O:17].C(=O)([O-])[O-].[K+].[K+]>O1CCCC1>[N+:16]([C:19]1[CH:24]=[CH:23][C:22]([S:25][C:2]2[C:3]([S:25][C:22]3[CH:23]=[CH:24][C:19]([N+:16]([O-:18])=[O:17])=[CH:20][CH:21]=3)=[C:4]([S:25][C:22]3[CH:23]=[CH:24][C:19]([N+:16]([O-:18])=[O:17])=[CH:20][CH:21]=3)[C:5]([S:25][C:22]3[CH:23]=[CH:24][C:19]([N+:16]([O-:18])=[O:17])=[CH:20][CH:21]=3)=[C:6]3[C:11](=[O:12])[NH:10][C:8](=[O:9])[C:7]=23)=[CH:21][CH:20]=1)([O-:18])=[O:17]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 158094-NitrobenzenethiolHCID 740773,4,5,6-Tetrachlorophthalimide

Product 1

HCID 20269595Tetrakis-(p-nitrophenylthio)-phthalimide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2 g (7.02 millimols) of tetrachlorophthalimide, 4.36 g (28.08 millimols) of p-nitrothiophenol, 5.82 g (42.12 millimols) of potassium carbonate and 30 ml of tetrahydrofuran are stirred at 25° C. for 14 hours. The mixture is acidified and extracted with tetrahydrofuran/toluene and the extracts are dried and evaporated. The residue is washed with methylene chloride and recrystallised from dioxane/toluene. This yields 3.02 g (57% of theory) of tetrakis-(p-nitrophenylthio)-phthalimide; melting point 297°-301° C.

Workup

  1. extractionextracted with tetrahydrofuran/toluene
  2. customthe extracts are dried
  3. customevaporated
  4. washThe residue is washed with methylene chloride
  5. customrecrystallised from dioxane/toluene

Sources & evidence

ORD record
ord-7ab8869127a04d5fa6892289d1d3f937
Source dataset
uspto-grants-1984_07
Patent number
US04459414

Reaction notes

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