Sodium Iodide → HCID 21877079, compound

HRID 353096Notes

Reaction equation

HRID 353096 reaction equation
Cl[CH:2]([C:10](=[O:13])[CH2:11][CH3:12])[C:3](=[O:9])[C:4]([O:6][CH2:7][CH3:8])=[O:5].[Cl:14][C:15]1[CH:16]=[C:17]([SH:22])[CH:18]=[C:19]([Cl:21])[CH:20]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>CC(C)=O.O>[Cl:14][C:15]1[CH:16]=[C:17]([S:22][CH:2]([C:10](=[O:13])[CH2:11][CH3:12])[C:3](=[O:9])[C:4]([O:6][CH2:7][CH3:8])=[O:5])[CH:18]=[C:19]([Cl:21])[CH:20]=1

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 27360963,5-DichlorobenzenethiolHCID 3006758ethyl 3-chloro-2,4-dioxohexanoate

Product 1

HCID 21877079HCID 21877079, compoundYield 102.4%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

A solution of ethyl 3-chloro-2,4-dioxohexanoate (EP117082 A2) (7.10 g, 34.4 mmol) in acetone (175 ml) was treated with 3,5-dichlorothiophenol (6.16 g, 34.4 mmol), potassium carbonate (5.22 g, 37.8 mmol) and sodium iodide (5.16 g, 34.4 mmol) and the resulting mixture was stirred at room temperature for 18 hours. The reaction mixture was diluted with water (70 ml) and concentrated under reduced pressure. The residue was diluted with 2M aqueous hydrochloric acid (70 ml) and extracted with dichloromethane (3×150 ml). The combined organic extracts were dried over anhydrous magnesium sulphate, filtered and concentrated under reduced pressure. The crude product was purified by flash chromatography on silica gel eluting with a solvent gradient of cyclohexane:ethyl acetate (3:1, by volume) gradually changing to cyclohexane:ethyl acetate (1:1, by volume) to afford the title compound (12.3 g) as a red oil.

Workup

  1. concentrationconcentrated under reduced pressure
  2. additionThe residue was diluted with 2M aqueous hydrochloric acid (70 ml)
  3. extractionextracted with dichloromethane (3×150 ml)
  4. dry with materialThe combined organic extracts were dried over anhydrous magnesium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude product was purified by flash chromatography on silica gel eluting with a solvent gradient of cyclohexane:ethyl acetate (3:1, by volume)

Sources & evidence

ORD record
ord-f108a001ac59439bbfc5d39ddb61f94f
Source dataset
uspto-grants-2004_06
Patent number
US06750230B2

Reaction notes

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