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

HRID 1079449Notes

Reaction equation

HRID 1079449 reaction equation
[Cl:1][C:2]1[CH:12]=[CH:11][CH:10]=[CH:9][C:3]=1[O:4][CH2:5][C:6]([OH:8])=O.[N+]([O-])(O)=O.[O:17]([CH2:21][CH2:22][NH2:23])[N+:18]([O-:20])=[O:19].C(OC(C)C)(C)C>>[O:17]([CH2:21][CH2:22][NH:23][C:6](=[O:8])[CH2:5][O:4][C:3]1[CH:9]=[CH:10][CH:11]=[CH:12][C:2]=1[Cl:1])[N+:18]([O-:20])=[O:19]

Participants

4

Reactant 3

HCID 7914Diisopropyl EtherHCID 119692-Chlorophenoxyacetic acidHCID 78397Ethanol, 2-amino-, 1-nitrate, nitrate (1:1)

Product 1

HCID 15839959N-(2-Nitroxyethyl)-2-chlorophenoxyacetamideYield 31.8%

Procedure

Following a similar treatment to that in Example 2 and using 0.79 g of 2-chlorophenoxyacetic acid and 0.6 g of 2-nitroxyethylamine nitrate, 0.31 g of the title compound was obtained as colorless acicular prisms (solvent for recrystallization; diisopropyl ether).

Sources & evidence

ORD record
ord-86e39adc5cf340df89beffa4dbab0fd4
Source dataset
uspto-grants-1996_12
Patent number
US05580893

Reaction notes

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