Sodium Chloride → N-(2-Pyridinylmethyl)-N-[[4-(tetradecyloxy)phenyl]methyl]methanesulfonamide

HRID 248023

Reaction equation

HRID 248023 reaction equation
[H-].[Na+].[N:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9][NH:10][S:11]([CH3:14])(=[O:13])=[O:12].Br[CH2:16][C:17]1[CH:22]=[CH:21][C:20]([O:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])=[CH:19][CH:18]=1.[Cl-].[Na+]>O1CCCC1>[N:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9][N:10]([CH2:16][C:17]1[CH:22]=[CH:21][C:20]([O:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])=[CH:19][CH:18]=1)[S:11]([CH3:14])(=[O:13])=[O:12]

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 24758Sodium hydrideHCID 4657001N-(pyridin-2-ylmethyl)methanesulfonamideHCID 100228401-(Bromomethyl)-4-(tetradecyloxy)benzene

Product 1

HCID 19014986N-(2-Pyridinylmethyl)-N-[[4-(tetradecyloxy)phenyl]methyl]methanesulfonamideYield 38.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

To a room temperature slurry of 0.391 g of 50% sodium hydride in 20 ml of dry tetrahydrofuran is added, via cannula, 1.27 g of product from Example 121 in 30 ml of dry tetrahydrofuran. The reaction is stirred at room temperature for 1.5 hours. Two and one half grams of product from Example 20 in 30 ml of dry tetrahydrofuran is added via cannula. The reaction is stirred at room temperature for 20 hours followed by heating at reflux temperature for 2 hours. The cooled reaction is poured into half saturated sodium chloride and extracted with methylene chloride. The combined organic layers are washed with saturated sodium chloride, dried and concentrated in vacuo. The residue is purified by chromatography (silica gel: 40% ethyl acetate/hexane) to give 1.22 g of the desired product as colorless crystals.

Workup

  1. stirringThe reaction is stirred at room temperature for 20 hours
  2. temperatureby heating
  3. temperatureat reflux temperature for 2 hours
  4. customThe cooled reaction
  5. extractionextracted with methylene chloride
  6. washThe combined organic layers are washed with saturated sodium chloride
  7. customdried
  8. concentrationconcentrated in vacuo
  9. customThe residue is purified by chromatography (silica gel: 40% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-81fb874163f54816a4261f6a54b2ed94
Source dataset
uspto-grants-1993_05
Patent number
US05208247

Linked notes

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