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

HRID 840192Notes

Reaction equation

HRID 840192 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 with 3 ml of benzylamine and 100 ml of ammonium chloride for 3 hours at 130° C., cooled, taken up in 50 ml of chloroform and washed in sequence with water, dilute hydrochloric acid, aqueous bicarbonate solution and again with water. The crude product obtained after evaporating off the solvent is purified column chromatographically. 3-nitryloxy-2,2-bis(nitryloxymethyl)propionic acid N-benzylamide is obtained as a colourless oil. Yield: 73%.

Workup

  1. temperaturecooled
  2. washwashed in sequence with water, dilute hydrochloric acid, aqueous bicarbonate solution and again with water
  3. customThe crude product obtained
  4. customafter evaporating off the solvent
  5. customis purified column chromatographically

Sources & evidence

ORD record
ord-437a19c7e9c648319fc4ffaaba30cfb3
Source dataset
uspto-grants-2002_04
Patent number
US06365611B1

Reaction notes

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