Dimethylformamide → HCID 16046253, compound

HRID 1009177Notes

Reaction equation

HRID 1009177 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][NH:12][C:11](=[O:15])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].CN(C=O)C.[Cl:23][C:24]1[CH:31]=[CH:30][CH:29]=[CH:28][C:25]=1[CH2:26]Cl>ClCCl.O>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][N:12]([CH2:26][C:25]2[CH:28]=[CH:29][CH:30]=[CH:31][C:24]=2[Cl:23])[C:11](=[O:15])[CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 119062-Chlorobenzyl chlorideHCID 24758Sodium hydrideHCID 36077244-Benzyloxy-2(1H)-pyridone

Product 1

HCID 16046253HCID 16046253, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 4-benzyloxy-1H-pyridone (300 mg, 1.49 mmol) and NaH (60 mg, 1.49 mmol) in solvent of DMF was stirred for 30 min followed by adding 2-chlorobenzyl chloride (240 mg, 1.49 mmol) further stirring for 30 min at room temperature. The resulting solution was worked up with Water and dichloromethane and purified by column chromatography (ethyl acetate/hexane, 1:1) to obtain the titled compound (320 mg, 67%).

Workup

  1. custompurified by column chromatography (ethyl acetate/hexane, 1:1)

Sources & evidence

ORD record
ord-ec335de52c5c45fdbcc303b5c450145e
Source dataset
uspto-grants-2011_07
Patent number
US07973060B2

Reaction notes

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