Benzylamine → 3-nitryloxy-2,2-bis(nitryloxymethyl)propionic acid N-benzylamide

HRID 567931Notes

Reaction equation

HRID 567931 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].[CH2:21]([NH2:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.[Cl-].[NH4+]>C(Cl)(Cl)Cl>[CH2:21]([NH:28][C:7](=[O:8])[C:6]([CH2:16][O:17][N+:18]([O-:20])=[O:19])([CH2:11][O:12][N+:13]([O-:15])=[O:14])[CH2:5][O:4][N+:1]([O-:3])=[O:2])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 7504BenzylamineHCID 25517Ammonium ChlorideHCID 15380869Methyl 2,2-bis(nitryloxymethyl)-3-nitryloxypropionate

Product 1

HCID 153808733-nitryloxy-2,2-bis(nitryloxymethyl)propionic acid N-benzylamideYield 73%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

1 g (3.5 mmol) of methyl 3-nitryloxy-2,2-bis(nitryloxymethyl)propionate is heated for 3 hours at 130° C. with 3 ml of benzylamine and 100 mg of ammonium chloride and the mixture is cooled, taken up in 50 ml of chloroform and washed successively with water, with dilute hydrochloric acid, with aqueous bicarbonate solution and again with water. The crude product obtained after evaporation of the solvent is purified by column chromatography to give 3-nitryloxy-2,2-bis(nitryloxymethyl)propionic acid N-benzylamide (Tri-PA-NBzl amide) as a colourless oil. Yield: 73%. Elemental analysis: (C: conforms, H: conforms, N: conforms).

Workup

  1. temperaturethe mixture is cooled
  2. washwashed successively with water, with dilute hydrochloric acid, with aqueous bicarbonate solution and again with water
  3. customThe crude product obtained
  4. customafter evaporation of the solvent
  5. customis purified by column chromatography

Sources & evidence

ORD record
ord-42b3caafe9644876880c5feba7dc3b9d
Source dataset
uspto-grants-2001_01
Patent number
US06180664B2

Reaction notes

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