Diisopropyl Ether → N-(2-Nitroxyethyl)phenylthioacetamide

HRID 1079458Notes

Reaction equation

[C:1]1([CH2:7][C:8](O)=[S:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N+]([O-])(O)=O.[O:15]([CH2:19][CH2:20][NH2:21])[N+:16]([O-:18])=[O:17].C(OC(C)C)(C)C>>[O:15]([CH2:19][CH2:20][NH:21][C:8](=[S:9])[CH2:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[N+:16]([O-:18])=[O:17]

Participants

Reactant 3

HCID 7914Diisopropyl Ether

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

HCID 178526157HCID 178526157, compound

Product 1

HCID 86750043N-(2-Nitroxyethyl)phenylthioacetamideYield 66.9%

Procedure

Following a similar treatment to that in Example 2 and using 0.72 g of phenylthioacetic acid and 0.60 g of 2-nitroxyethylamine nitrate, 0.57 g of the title compound was obtained as colorless powdery crystals (solvent for recrystallization; diisopropyl ether).

Sources & evidence

ORD record: ord-229cd61738d8413287cc82aeb51f2c4b
Source dataset: uspto-grants-1996_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05580893

Reaction notes

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