Sodium hydride → N-Acetyl-4-(decyloxy)-3-(1,1-dimethylethyl)-N-(3-pyridinylmethyl)benzamide

HRID 248033Notes

Reaction equation

HRID 248033 reaction equation
[CH3:1][C:2]([C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][C:13]=1[O:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]CCCC)[C:8](Cl)=[O:9])([CH3:4])[CH3:3].[H-].[Na+].[N:31]1[CH:36]=[CH:35][CH:34]=[C:33]([CH2:37][NH:38][C:39](=[O:41])[CH3:40])[CH:32]=1>O1CCCC1>[C:39]([N:38]([CH2:37][C:33]1[CH:32]=[N:31][CH:36]=[CH:35][CH:34]=1)[C:8](=[O:9])[C:7]1[CH:11]=[CH:12][C:13]([O:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])=[C:5]([C:2]([CH3:1])([CH3:3])[CH3:4])[CH:6]=1)(=[O:41])[CH3:40]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 27352253-(Acetamidomethyl)pyridineHCID 190153703-(1,1-Dimethylethyl)-4-(tetradecyloxy)benzoyl chloride

Product 1

HCID 19015040N-Acetyl-4-(decyloxy)-3-(1,1-dimethylethyl)-N-(3-pyridinylmethyl)benzamideYield 176.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The title compound is prepared by the procedure of Example 27, using 0.90 g of product from Example 33, 0.316 g of washed 50% sodium hydride, 2.57 g of product from Example 14 and 25 ml of dry tetrahydrofuran. The residue is purified by chromatography (silica gel: 40% ethyl acetate/hexane) to give 1.81 g of the desired product as a yellow oil which crystallizes on standing.

Workup

  1. customThe title compound is prepared by the procedure of Example 27
  2. customThe residue is purified by chromatography (silica gel: 40% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-1579ec90327a4b159e9d9f2a3956f563
Source dataset
uspto-grants-1993_05
Patent number
US05208247

Reaction notes

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