Sodium hydride → N-Acetyl-4-methoxy-3-(tetradecyloxy)-N-(2-pyridinylmethyl)benzamide

HRID 247953Notes

Reaction equation

HRID 247953 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:6]([C:7](Cl)=[O:8])=[CH:5][C:4]=1[O: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][CH2:25][CH3:26].[N:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[CH2:33][NH:34][C:35](=[O:37])[CH3:36].[H-].[Na+]>O1CCCC1>[C:35]([N:34]([CH2:33][C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][N:27]=1)[C:7](=[O:8])[C:6]1[CH:10]=[CH:11][C:3]([O:2][CH3:1])=[C:4]([O: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][CH2:25][CH3:26])[CH:5]=1)(=[O:37])[CH3:36]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 5084090N-(pyridin-2-ylmethyl)acetamideHCID 19016259HCID 19016259, compound

Product 1

HCID 10255296N-Acetyl-4-methoxy-3-(tetradecyloxy)-N-(2-pyridinylmethyl)benzamideYield 30.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The title compound is prepared by the procedure of Example 27 using 1.19 g of product from Example 43, 0.490 g of product from Example 12, 0.157 g of washed 50% sodium hydride and 12 ml of tetrahydrofuran. The residue is purified by column chromatography (silica gel:35% ethyl acetate/hexane) to give 0.472 g of the desired product as yellow crystals.

Workup

  1. customThe residue is purified by column chromatography (silica gel:35% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-c65ddea7c0494feca540ea946325f21f
Source dataset
uspto-grants-1993_05
Patent number
US05208247

Reaction notes

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