Hydrochloric Acid → HCID 9883399, compound

HRID 1873234Notes

Reaction equation

HRID 1873234 reaction equation
[C:1]([CH2:4][C:5]1[CH:6]=[C:7]([CH:12]([CH3:16])[C:13]([OH:15])=[O:14])[CH:8]=[CH:9][C:10]=1I)([OH:3])=[O:2].C(=O)([O-])[O-].[K+].[K+].[C:23]1([SH:29])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.Cl>[Cu].CCCCCC.C(OCC)(=O)C.C(O)(=O)C.CN(C)C=O>[C:1]([CH2:4][C:5]1[CH:6]=[C:7]([CH:12]([CH3:16])[C:13]([OH:15])=[O:14])[CH:8]=[CH:9][C:10]=1[S:29][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)([OH:3])=[O:2]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 7969ThiophenolHCID 11430Potassium CarbonateHCID 15480018HCID 15480018, compound

Product 1

HCID 9883399HCID 9883399, compoundYield 49%

Reagents, catalysts & solvents 3

HCID 23978CopperCatalystHCID 6228DimethylformamideSolventHCID 21901998Ethyl acetate hexane acetic acidSolvent

Conditions

Temperature
115 °C

Procedure

2-(3-Carboxymethyl-4-iodophenyl)propionic acid (prepared in the manner as described in Example 12, 202 mg, 0.605 mol.), potassium carbonate (380 mg, 2.8 mmol.), N,N-dimethylformamide (DMF, 10 mL), and thiophenol (95 wt. %, 92 mg, 0.79 mmol.) were mixed. The resulting mixture was heated for 19 hours under reflux (temperature: approx. 115° C.) after addition of 20 mg of powdery copper. The reaction mixture was cooled, made acidic by addition of hydrochloric acid, and extracted with ethyl acetate. The ethyl acetate portion was washed with an aqueous sodium chloride solution, dried over magnesium sulfate, and concentrated to leave a residue. The residue was subjected to silica gel column chromatography (Wako gel C-200, Wako Jyunyaku Industry Co., Ltd., hexane/ethyl acetate/acetic acid=7/3/1, v/v/v) to obtain 94 mg (0.30 mmol., yield: 49%) of the desired compound.

Workup

  1. temperatureThe resulting mixture was heated for 19 hours
  2. temperatureThe reaction mixture was cooled
  3. extractionextracted with ethyl acetate
  4. washThe ethyl acetate portion was washed with an aqueous sodium chloride solution
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated
  7. customto leave a residue

Sources & evidence

ORD record
ord-40fc244277854a8b8cd27a89da286b56
Source dataset
uspto-grants-2000_08
Patent number
US06111115

Reaction notes

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