1,3-Diazido-2-propanol → 1,3-Diazido-2-propyl 4,4,4-Trinitrobutyrate
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
Product 1
Reagents, catalysts & solvents 1
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).