Myristyl bromide → N,N-Diethyl-2-(tetradecyloxy)benzamide

HRID 247928

Reaction equation

HRID 247928 reaction equation
[CH2:1]([N:3]([CH2:13][CH3:14])[C:4](=[O:12])[C:5]1[C:6](=[CH:8][CH:9]=[CH:10][CH:11]=1)[OH:7])[CH3:2].Br[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29].C(=O)([O-])[O-].[K+].[K+]>CC(=O)CC>[CH2:13]([N:3]([CH2:1][CH3:2])[C:4](=[O:12])[C:5]1[CH:11]=[CH:10][CH:9]=[CH:8][C:6]=1[O:7][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH3:16])[CH3:14]

Participants

5

Reactant 3

HCID 8208Myristyl bromideHCID 11430Potassium CarbonateHCID 88006Diethylsalicylamide

Product 1

HCID 19016298N,N-Diethyl-2-(tetradecyloxy)benzamide

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of 25 g of N,N-diethylsalicylamide, 38.5 ml of 1-bromotetradecane, 22.35 g of potassium carbonate and 400 ml of 2-butanone is heated at reflux temperature for 16 hours. The reaction is cooled, filtered and concentrated in vacuo. The concentrate is dissolved in chloroform, dried and concentrated in vacuo. The residue is purified by column chromatography (silica gel:0-30% ethyl acetate/hexane) to give 42.5 g of the desired product as colorless crystals.

Workup

  1. temperatureis heated
  2. temperatureat reflux temperature for 16 hours
  3. temperatureThe reaction is cooled
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. dissolutionThe concentrate is dissolved in chloroform
  7. customdried
  8. concentrationconcentrated in vacuo
  9. customThe residue is purified by column chromatography (silica gel:0-30% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-abd0eef33caf43baafbb8f4403bcda70
Source dataset
uspto-grants-1993_05
Patent number
US05208247

Linked notes

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