Thiophenol → 7-Phenyl-3-phenylsulfanylheptanoic acid hydroxyamide

HRID 1107107Notes

Reaction equation

HRID 1107107 reaction equation
[OH:1][NH:2][C:3](=[O:16])[CH:4]=[CH:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[C:17]1([SH:23])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.N1CCCCC1>O1CCOCC1>[OH:1][NH:2][C:3](=[O:16])[CH2:4][CH:5]([S:23][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH2:6][CH2:7][CH2:8][CH2:9][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 7969ThiophenolHCID 8082PiperidineHCID 54264321HCID 54264321, compound

Product 1

HCID 179155207-Phenyl-3-phenylsulfanylheptanoic acid hydroxyamide

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
85 °C

Procedure

7-Phenyl-hept-2-enoic acid hydroxyamide (0.3 g; 1.4 mmol) is combined with thiophenol (0.26 g; 2.4 mmol) and piperidine (0.04 g; 0.5 mmol) in 1,4-dioxane (6 mL) and heated to 85° C. for 4 hours. After cooling, the reaction is concentrated in vacuo and purified by column chromatography using 5% MeOH/CH2Cl2 to obtain 7-phenyl-3-phenylsulfanylheptanoic acid hydroxyamide.

Workup

  1. temperatureAfter cooling
  2. concentrationthe reaction is concentrated in vacuo
  3. custompurified by column chromatography

Sources & evidence

ORD record
ord-7fc4d67d825842479982e4486828d6ef
Source dataset
uspto-grants-2000_05
Patent number
US06057369

Reaction notes

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