1,3-Diazido-2-propanol → 1,3-Diazido-2-propyl 4,4,4-Trinitrobutyrate

HRID 1391267Notes

Reaction equation

HRID 1391267 reaction equation
[N+:1]([C:4]([N+:13]([O-:15])=[O:14])([N+:10]([O-:12])=[O:11])[CH2:5][CH2:6][C:7](Cl)=[O:8])([O-:3])=[O:2].[N:16]([CH2:19][CH:20]([OH:25])[CH2:21][N:22]=[N+:23]=[N-:24])=[N+:17]=[N-:18]>C(Cl)CCl>[N+:1]([C:4]([N+:13]([O-:15])=[O:14])([N+:10]([O-:12])=[O:11])[CH2:5][CH2:6][C:7]([O:25][CH:20]([CH2:21][N:22]=[N+:23]=[N-:24])[CH2:19][N:16]=[N+:17]=[N-:18])=[O:8])([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 1513671,3-Diazido-2-propanolHCID 125075564,4,4-Trinitrobutyryl chloride

Product 1

HCID 125075571,3-Diazido-2-propyl 4,4,4-TrinitrobutyrateYield 73.5%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A solution of 25g (0.1 mole) of 4,4,4-trinitrobutyryl chloride, 14.7g (0.1 mole) of 1,3-diazido-2-propanol, and 50 ml of ethylene dichloride was refluxed for one week. The solution was cooled, washed with water, dried, and concentrated to give 25.5g (73.5%) of amber liquid. The product was purified by dissolving in carbon tetrachloride and passing through a neutral alumina column. Concentration of this solution gave a yellow liquid, nD24 = 1.5029, d25 = 1.464. The infrared spectrum showed the expected strong absorption for azide (4.7μ), carbonyl (5.8μ), and nitro (6.2μ).

Workup

  1. temperatureThe solution was cooled
  2. washwashed with water
  3. customdried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-a426db02310a4804afefadc37c263017
Source dataset
uspto-grants-1979_02
Patent number
US04141910

Reaction notes

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