Sodium Iodide → 4-(Tetradecyloxy)benzamide

HRID 1728873Notes

Reaction equation

HRID 1728873 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH2:8])=[O:7])=[CH:4][CH:3]=1.Br[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25].[OH-].[K+].[I-].[Na+]>O.CN(C)C=O>[CH2:25]([O:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH2:8])=[O:7])=[CH:4][CH:3]=1)[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH3:12]

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 8208Myristyl bromideHCID 14797Potassium HydroxideHCID 650524-Hydroxybenzamide

Product 1

HCID 123614684-(Tetradecyloxy)benzamideYield 47.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 50 g of 4-hydroxybenzamide, 106.1 g of 1-bromotetradecane, 75.59 g of potassium hydroxide, 5.46 g of sodium iodide and 600 ml of dimethylformamide is heated at 110° C. for 24 hours; followed by stirring at room temperature for 72 hours. The reaction is poured into water, the resulting solid collected and washed with water. The solid is recrystallized first from chloroform then ethyl acetate to give 58 g of the desired product.

Workup

  1. customthe resulting solid collected
  2. washwashed with water
  3. customThe solid is recrystallized first from chloroform

Sources & evidence

ORD record
ord-4a5173b08e0d48dfbdfa5b0ed3f19c8c
Source dataset
uspto-grants-1994_07
Patent number
US05328921

Reaction notes

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