Sodium Iodide → 4-(3-Iodopropoxy)benzoic acid, methyl ester

HRID 1780786Notes

Reaction equation

HRID 1780786 reaction equation
S1C2C=CC=CC=2N=C1C(C1CCN([CH2:18][CH2:19][CH2:20][O:21][C:22]2[CH:31]=[CH:30][C:25]([C:26]([O:28][CH3:29])=[O:27])=[CH:24][CH:23]=2)CC1)=O.ClCCCOC1C=CC(C(OC)=O)=CC=1.[I-:47].[Na+]>CC(C)=O.C(OCC)C>[I:47][CH2:18][CH2:19][CH2:20][O:21][C:22]1[CH:31]=[CH:30][C:25]([C:26]([O:28][CH3:29])=[O:27])=[CH:24][CH:23]=1

Participants

6

Reactant 3

HCID 5238Sodium IodideHCID 12389265Methyl 4-(3-chloropropoxy)benzoateHCID 153374634-[3-[4-[(2-Benzothiazolyl)carbonyl]-1-piperidinyl]propoxy]benzoic acid methyl ester

Product 1

HCID 153374624-(3-Iodopropoxy)benzoic acid, methyl ester

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 3283Diethyl EtherSolvent

Procedure

4-[3-[4-[(2-Benzothiazolyl)carbonyl]-1-piperidinyl]propoxy]benzoic acid, methyl ester ##STR22## Dissolve 4-(3-chloropropoxy)benzoic acid, methyl ester (6.97 g, 30.5 mmol) in anhydrous acetone (100 mL) and add powdered sodium iodide (16.0 g, 107 mmol). Heat at reflux under an argon atmosphere for 38 hours. Dilute with ethyl ether (100 mL) and filter through Celite® filter aid. Wash the filtrate with water and brine, then dry (MgSO4). Evaporate the solvent in vacuo to give 4-(3-iodopropoxy)benzoic acid, methyl ester as a yellow oil.

Workup

  1. temperatureHeat
  2. temperatureat reflux under an argon atmosphere for 38 hours
  3. filtrationfilter through Celite®
  4. filtrationfilter aid
  5. washWash the filtrate with water and brine
  6. dry with materialdry (MgSO4)
  7. customEvaporate the solvent in vacuo

Sources & evidence

ORD record
ord-b55a5b56ecd6472eb1f52e0aa86fe4a7
Source dataset
uspto-grants-1997_05
Patent number
US05631268

Reaction notes

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