Sodium hydride → 4-Methyl-N-(2-pyridinylmethyl)-N-[[3-(tetradecyloxy)phenyl]methyl]benzenesulfonamide

HRID 247988Notes

Reaction equation

HRID 247988 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.Br[CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([O:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41])[CH:22]=1.[H-].[Na+]>O1CCCC1>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([N:11]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=2)[CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([O:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41])[CH:22]=2)(=[O:9])=[O:10])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 7316234-Methyl-N-pyridin-2-ylmethyl-benzenesulfonamideHCID 99772501-(Bromomethyl)-3-(tetradecyloxy)benzene

Product 1

HCID 190162644-Methyl-N-(2-pyridinylmethyl)-N-[[3-(tetradecyloxy)phenyl]methyl]benzenesulfonamideYield 45.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The title compound is prepared by the procedure of Example 27, using 1.23 g of product from Example 79, 1.71 g of product from Example 25, 0.321 g of washed 50% sodium hydride and 70 ml of tetrahydrofuran. The reaction is stirred at room temperature for 68 hours. The residue is purified by column chromatography (silica gel: 25% ethyl acetate/hexane) to give 1.15 g of the desired product as a colorless oil, which crystallized on standing.

Workup

  1. customThe title compound is prepared by the procedure of Example 27
  2. customThe residue is purified by column chromatography (silica gel: 25% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-cd2b31ee2ae84180b51b3facfa160b63
Source dataset
uspto-grants-1993_05
Patent number
US05208247

Reaction notes

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