Sodium Iodide → 4-(Tetradecyloxy)benzamide

HRID 248006Notes

Reaction equation

HRID 248006 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-e06d1589eb534c1e94eb74f9334fc359
Source dataset
uspto-grants-1993_05
Patent number
US05208247

Reaction notes

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