Hydrochloric Acid → 3-Nitryloxy-2,2-bis(nitryloxymethyl)propionic acid hydrazide

HRID 567932Notes

Reaction equation

HRID 567932 reaction equation
[N+:1]([O:4][CH2:5][C:6]([CH2:16][O:17][N+:18]([O-:20])=[O:19])([CH2:11][O:12][N+:13]([O-:15])=[O:14])[C:7](OC)=[O:8])([O-:3])=[O:2].Cl.[NH2:22][NH2:23].Cl>>[N+:1]([O:4][CH2:5][C:6]([CH2:16][O:17][N+:18]([O-:20])=[O:19])([CH2:11][O:12][N+:13]([O-:15])=[O:14])[C:7]([NH:22][NH2:23])=[O:8])([O-:3])=[O:2]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 115031Hydrazinium chlorideHCID 15380869Methyl 2,2-bis(nitryloxymethyl)-3-nitryloxypropionate

Product 1

HCID 153808743-Nitryloxy-2,2-bis(nitryloxymethyl)propionic acid hydrazideYield 63%

Procedure

1 g (3.5 mmol) of methyl 2,2-bis(nitryloxymethyl)-3-nitryloxypropionate is heated for 5 hours in a water bath with excess aqueous hydrazine hydrochloride solution. The mixture is poured onto ice and weakly acidified with hydrochloric acid. The oil which has deposited is separated by column chromatography to give 3-nitryloxy-2,2-bis(nitryloxymethyl)propionic acid hydrazide (Tri-PA hydrazide) as a colourless oil. Yield: 63%. Elemental analysis: (C: conforms, H: conforms, N: conforms).

Workup

  1. additionThe mixture is poured onto ice
  2. customThe oil which has deposited is separated by column chromatography

Sources & evidence

ORD record
ord-907267379249417fb39aad15005fd53e
Source dataset
uspto-grants-2001_01
Patent number
US06180664B2

Reaction notes

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