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p-Chlorothiophenol → 6-(4-Chlorophenylsulfanyl)-hexylphthalimide

HRID 2097361
Notes
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Reaction equation

HRID 2097361 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([SH:8])=[CH:4][CH:3]=1.BrCCCCCC[N:16]1[C:20](=[O:21])[C:19]2=[CH:22][CH:23]=[CH:24][CH:25]=[C:18]2[C:17]1=[O:26].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH2:6][CH2:7][CH2:2][CH2:3][CH2:4][CH2:5][C:25]2[CH:24]=[CH:23][CH:22]=[C:19]3[C:20]([NH:16][C:17](=[O:26])[C:18]=23)=[O:21])=[CH:4][CH:3]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 7815p-ChlorothiophenolHCID 11430Potassium CarbonateHCID 141120N-(6-Bromohexyl)phthalimide

Product 1

HCID 866225746-(4-Chlorophenylsulfanyl)-hexylphthalimide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

4-Chlorothiophenol (2.89 g, 20 mmol), N-(6-bromohexyl)-phthalimide (6.20 g, 20 mmol) and K2CO3 (5.53 g, 40 mmol) were suspended in DMF (50 mL) under an atmosphere of argon and stirred at 90° C. for 23 h. The solvent was evaporated under reduced pressure and the residue was partitioned between water (100 mL) and CH2Cl2 (150 mL). The aqueous layer was extracted with CH2Cl2 (2×100 mL), the combined org. layers were dried over Na2SO4, filtered and the solvent was removed under reduced pressure to give the title compound, pure enough for further reactions.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. customthe residue was partitioned between water (100 mL) and CH2Cl2 (150 mL)
  3. extractionThe aqueous layer was extracted with CH2Cl2 (2×100 mL)
  4. dry with materiallayers were dried over Na2SO4
  5. filtrationfiltered
  6. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-2987f79b79ab4f438c4117417e1cc34e
Source dataset
uspto-grants-2013_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08450348B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes