Thiophenol → HCID 178449353, compound

HRID 485963Notes

Reaction equation

HRID 485963 reaction equation
[CH2:1]([N:5]=[C:6]([OH:20])[C:7]1[C:8](=[C:12]([Cl:19])[C:13](Cl)=[C:14](Cl)[C:15]=1[Cl:16])[C:9]([OH:11])=[O:10])[CH2:2][CH2:3][CH3:4].C(=O)([O-])[O-].[K+].[K+].[C:27]1([SH:33])[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>O1CCCC1>[CH2:1]([N:5]=[C:6]([OH:20])[C:7]1[C:8](=[C:12]([Cl:19])[C:13]([S:33][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[C:14]([S:33][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:15]=1[Cl:16])[C:9]([OH:11])=[O:10])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 7969ThiophenolHCID 11430Potassium CarbonateHCID 178449351HCID 178449351, compound

Product 1

HCID 178449353HCID 178449353, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

20 g (58.65 millimols) of tetrachlorophthalic acid N-n-butylimide, 33.64 g (243 millimols) of potassium carbonate, 13.57 g (123 millimols) of thiophenol and 150 ml of tetrahydrofuran are stirred at 25° C. for 18 hours. The mixture is acidified and extracted with methylene chloride. The extracts are dried and evaporated. After recrystallisation from toluene/cyclohexane, 23.88 g (83% of theory) of 4,5-bis-(phenylthio)-3,6-dichlorophthalic acid N-n-butylimide are obtained; melting point 215°-6° C.

Workup

  1. extractionextracted with methylene chloride
  2. customThe extracts are dried
  3. customevaporated
  4. customAfter recrystallisation from toluene/cyclohexane, 23.88 g (83% of theory) of 4,5-bis-(phenylthio)-3,6-dichlorophthalic acid N-n-butylimide
  5. customare obtained

Sources & evidence

ORD record
ord-748846dc959e4f7980cc566a49e2155c
Source dataset
uspto-grants-1985_08
Patent number
US04537977

Reaction notes

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