Sodium Iodide → HCID 15341832, compound

HRID 893472Notes

Reaction equation

HRID 893472 reaction equation
[OH:1][C:2]1[C:10]([CH2:11][CH:12]=[CH2:13])=[C:9]([OH:14])[CH:8]=[CH:7][C:3]=1[C:4]([NH2:6])=[O:5].Cl[CH2:16][CH2:17][CH2:18][O:19][C:20]1[C:21]([CH2:33][CH2:34][CH3:35])=[C:22]([CH:30]=[CH:31][CH:32]=1)[O:23][CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26].[I-].[Na+].C(=O)([O-])[O-].[K+].[K+]>C(OCC)(=O)C.CCCCCC.O.CN(C=O)C>[NH2:6][C:4]([C:3]1[CH:7]=[CH:8][C:9]([O:14][CH2:16][CH2:17][CH2:18][O:19][C:20]2[C:21]([CH2:33][CH2:34][CH3:35])=[C:22]([CH:30]=[CH:31][CH:32]=2)[O:23][CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])=[C:10]([CH2:11][CH:12]=[CH2:13])[C:2]=1[OH:1])=[O:5]

Participants

8

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 15341803HCID 15341803, compoundHCID 15341816HCID 15341816, compound

Product 1

HCID 15341832HCID 15341832, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 21226206Ethyl acetate hexaneSolvent

Conditions

Temperature
40 °C

Procedure

2,4-Dihydroxy-3-(2-propenyl)benzamide(193 mg 1.0 mmol), ethyl [3-(3-chloropropoxy)-2-propylphenoxy]acetate(386 mg, 1.0 mmol), sodium iodide (276 mg, 2.0 mmol), and potassium carbonate (276 mg, 2.0 mmol) were added to 2.0 ml of DMF, and the reaction mixture was heated in an oil bath at 40° C. overnight. The temperature was raised to 60° C., and the reaction mixture was again heated overnight. The reaction mixture was poured into 15 ml of water and extracted three times with ethyl acetate. The combined extracts were washed twice with water, dried and filtered. The solvent was removed under vacuum to give the crude product as a solid. Chromatography of the crude product on silica gel with 50/50 ethyl acetate/hexane as eluant gave the product.

Workup

  1. temperatureThe temperature was raised to 60° C.
  2. extractionextracted three times with ethyl acetate
  3. washThe combined extracts were washed twice with water
  4. customdried
  5. filtrationfiltered
  6. customThe solvent was removed under vacuum
  7. customto give the crude product as a solid

Sources & evidence

ORD record
ord-fb6c6f9944194ebe95836275732bca14
Source dataset
uspto-grants-1992_06
Patent number
US05124350

Reaction notes

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