4-Methylbenzenethiol → Tetrakis-(p-toluylthio)-phthalic acid N-2-hydroxyethylimide

HRID 1462266Notes

Reaction equation

HRID 1462266 reaction equation
[OH:1][CH2:2][CH2:3][N:4]=[C:5]([OH:19])[C:6]1[C:7](=[C:11](Cl)[C:12](Cl)=[C:13](Cl)[C:14]=1Cl)[C:8]([OH:10])=[O:9].[CH3:20][C:21]1[CH:26]=[CH:25][C:24]([SH:27])=[CH:23][CH:22]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[OH:1][CH2:2][CH2:3][N:4]=[C:5]([OH:19])[C:6]1[C:7](=[C:11]([S:27][C:24]2[CH:25]=[CH:26][C:21]([CH3:20])=[CH:22][CH:23]=2)[C:12]([S:27][C:24]2[CH:25]=[CH:26][C:21]([CH3:20])=[CH:22][CH:23]=2)=[C:13]([S:27][C:24]2[CH:25]=[CH:26][C:21]([CH3:20])=[CH:22][CH:23]=2)[C:14]=1[S:27][C:24]1[CH:25]=[CH:26][C:21]([CH3:20])=[CH:22][CH:23]=1)[C:8]([OH:10])=[O:9]

Participants

5

Reactant 3

HCID 78114-MethylbenzenethiolHCID 11430Potassium CarbonateHCID 178524541HCID 178524541, compound

Product 1

HCID 136429048Tetrakis-(p-toluylthio)-phthalic acid N-2-hydroxyethylimide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2 g (6.08 millimols) of tetrachlorophthalic acid N-2-hydroxyethylimide, 3.1 g (24.93 millimols) of p-thiocresol, 5.08 g (36.78 millimols) of potassium carbonate and 20 ml of N,N-dimethylformamide are stirred at 25° C. for 1 hour. After evaporation, the residue is acidified with dilute HCl solution and extracted with methylene chloride. After recrystallisation from toluene/cyclohexane, 3.21 g (78% of theory) of the title compound are obtained; melting point 161°-2° C.

Workup

  1. customAfter evaporation
  2. extractionextracted with methylene chloride
  3. customAfter recrystallisation from toluene/cyclohexane, 3.21 g (78% of theory) of the title compound
  4. customare obtained

Sources & evidence

ORD record
ord-627c99fa5d9f426f8dd836d4815d4aa6
Source dataset
uspto-grants-1984_07
Patent number
US04459414

Reaction notes

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