Diisopropyl Ether → N-(2-Nitroxyethyl)-2-methoxyphenoxyacetamide

HRID 1079460

Reaction equation

[CH3:1][O:2][C:3]1[CH:13]=[CH:12][CH:11]=[CH:10][C:4]=1[O:5][CH2:6][C:7]([OH:9])=O.[N+]([O-])(O)=O.[O:18]([CH2:22][CH2:23][NH2:24])[N+:19]([O-:21])=[O:20].C(OC(C)C)(C)C>>[O:18]([CH2:22][CH2:23][NH:24][C:7](=[O:9])[CH2:6][O:5][C:4]1[CH:10]=[CH:11][CH:12]=[CH:13][C:3]=1[O:2][CH3:1])[N+:19]([O-:21])=[O:20]

Participants

Reactant 3

HCID 7914Diisopropyl Ether

HCID 158822-(2-Methoxyphenoxy)acetic acid

HCID 78397Ethanol, 2-amino-, 1-nitrate, nitrate (1:1)

Product 1

HCID 15839972N-(2-Nitroxyethyl)-2-methoxyphenoxyacetamideYield 28.2%

Procedure

Following a similar treatment to that in Example 2 and using 0.77 g of 2-methoxyphenoxyacetic acid and 0.60 g of nitroxyethylamine nitrate, 0.27 g of the title compound was obtained as colorless needles (solvent for recrystallization; diisopropyl ether).

Sources & evidence

ORD record: ord-24d845c6e403449aac31a555488f88bb
Source dataset: uspto-grants-1996_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05580893

Linked notes

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