Sodium Iodide → HCID 21496591, compound

HRID 1730826Notes

Reaction equation

HRID 1730826 reaction equation
[CH2:1]([O:3][CH:4]([C:9]1[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=1)[CH2:5][CH2:6][CH2:7][NH2:8])[CH3:2].[CH2:16]([O:18][C:19]1[CH:28]=[CH:27][CH:26]=[CH:25][C:20]=1[O:21][CH2:22][CH2:23]Cl)[CH3:17].[I-].[Na+].[C:31](=[O:34])([OH:33])[O-].[Na+]>O.CN(C)C=O>[C:4]([OH:3])(=[O:18])[C:31]([OH:33])=[O:34].[CH2:1]([O:3][CH:4]([C:9]1[CH:10]=[CH:11][C:12]([F:15])=[CH:13][CH:14]=1)[CH2:5][CH2:6][CH2:7][NH:8][CH2:23][CH2:22][O:21][C:20]1[CH:25]=[CH:26][CH:27]=[CH:28][C:19]=1[O:18][CH2:16][CH3:17])[CH3:2]

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 516892Sodium BicarbonateHCID 176208991-(2-Chloroethoxy)-2-ethoxybenzeneHCID 21496608HCID 21496608, compound

Product 1

HCID 21496591HCID 21496591, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 2 g of N-[4-ethoxy-4-(4-fluorophenyl)butyl]amine, 2 g of 2-(2-ethoxyphenoxy)ethyl chloride, 0.1 g of sodium iodide, 1 g of sodium bicarbonate and 20 ml of N,N-dimethylformamide was stirred at about 110° C for 20 hours. After cooling, the reaction mixture was poured into 200 ml of water and extracted with benzene. The benzene layer was washed with water, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was treated with ethanolic oxalic acid and recrystallized from ethanol to give N-[4-ethoxy-4-(4-fluorophenyl)butyl]-2-(2-ethoxyphenoxy)ethylamine oxalate, M.P. 157° - 160° C.

Workup

  1. temperatureAfter cooling
  2. extractionextracted with benzene
  3. washThe benzene layer was washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. additionThe residue was treated with ethanolic oxalic acid
  7. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-5d7e3d0f06e64087ab01e7c6b1776fef
Source dataset
uspto-grants-1976_11
Patent number
US03993780

Reaction notes

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