Sodium hydride → N-(4-acetylphenyl)-N[2-(2-naphthalenyloxy)ethyl]formamide

HRID 2225760Notes

Reaction equation

[C:1]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][CH:11]=[O:12])=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[H-].[Na+].CS(O[CH2:20][CH2:21][O:22][C:23]1[CH:32]=[CH:31][C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:24]=1)(=O)=O>CN(C)C=O>[C:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]([CH2:20][CH2:21][O:22][C:23]2[CH:32]=[CH:31][C:30]3[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=3)[CH:24]=2)[CH:11]=[O:12])=[CH:6][CH:5]=1)(=[O:3])[CH3:2]

Participants

Conditions

Temperature: 60 °C

Procedure

A stirred mixture of N-(4-acetylphenyl)formamide (4.9 g) in dimethylformamide (50 mL) under argon was treated with 55% sodium hydride (1.31 g), stireed for 15 minutes and treated with 2-(2-naphthalenyloxy)ethyl methanesulfonate (7.6 g). The mixture was heated at 60° C. overnight and worked upas in Example 20. The material from dichloromethane extraction was purified by HPLC (dichloromethane-ethyl acetate; 20:1 ) and crystallized from dichloromethane-hexane to provide 5.9 g of N-(4-acetylphenyl)-N[2-(2-naphthalenyloxy)ethyl]formamide as a colorless solid, mp 115°-116° C.

Workup

extractionThe material from dichloromethane extraction
customwas purified by HPLC (dichloromethane-ethyl acetate; 20:1 )
customcrystallized from dichloromethane-hexane

Sources & evidence

ORD record: ord-fad3204514c8406f868041121e167961
Source dataset: uspto-grants-1994_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05344843

Reaction notes

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