Thiophenol → 9,10-Bis(phenylsulfanyl)anthracene

HRID 845714

Reaction equation

HRID 845714 reaction equation
[OH-].[K+].[C:3]1([SH:9])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Br[C:11]1[C:12]2[C:17]([C:18](Br)=[C:19]3[C:24]=1[CH:23]=[CH:22][CH:21]=[CH:20]3)=[CH:16][CH:15]=[CH:14][CH:13]=2>CC(N(C)C)=O>[S:9]([C:11]1[C:12]2[C:17]([C:18]([S:9][C:3]3[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=3)=[C:19]3[C:24]=1[CH:23]=[CH:22][CH:21]=[CH:20]3)=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 7969ThiophenolHCID 14797Potassium HydroxideHCID 682269,10-Dibromoanthracene

Product 1

HCID 125401919,10-Bis(phenylsulfanyl)anthracene

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
170 °C

Procedure

Potassium hydroxide (19.6 g) and thiophenol (35.5 ml) were heated at 170 degrees C. in dimethylacetamide for two hours. 9,10-dibromoanthracene (37.5 g) was added and the mixture heated at 170 degrees C. an additional two hours. (The corresponding dichloro compound has also been used successfully.) The mixture was quenched with water and the precipitate recrystallized from chloroform/ethanol to give DTPA.

Workup

  1. customan additional two hours
  2. custom) The mixture was quenched with water
  3. customthe precipitate recrystallized from chloroform/ethanol

Sources & evidence

ORD record
ord-c2e99d649db145909237e9c8f6db187f
Source dataset
uspto-grants-1988_07
Patent number
US04760013

Linked notes

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