Isobutylene → 1-Tertiarybutyl-3,3-dinitroazetidine hydrochloride
Reaction equation
[C:1]([N:5]1[CH2:8][C:7]([N+:12]([O-:14])=[O:13])([N+:9]([O-:11])=[O:10])[CH2:6]1)([CH3:4])([CH3:3])[CH3:2].[Cl:15]C(OCC1C=CC=CC=1)=O.CC(=C)C>C(Cl)(Cl)Cl>[ClH:15].[C:1]([N:5]1[CH2:6][C:7]([N+:12]([O-:14])=[O:13])([N+:9]([O-:11])=[O:10])[CH2:8]1)([CH3:4])([CH3:2])[CH3:3]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To 1-tertiary-butyl-3,3-dinitroazetidine (20 g, 0.099 mole) in 25 milliliters (ml) of chloroform was added benzyl chloroformate (9.24 g, 0.054 mole). The mixture was stirred under reflux for 24 hours during which time isobutylene was generated and a white precipitate was formed. The mixture was allowed to cool and was the precipitate was separated by filtration. The filter cake was washed with methylene chloride, air dried and weighed to yield 6.4 g (27%) of 1-tertiary-butyl-3,3-dinitroazetidine hydrochloride. The filtrate was evaporated under vacuum to yield a yellow solid. This solid was taken up in warm toluene, the mixture filtered while hot, and the filtrate treated with hexanes to crystallize the product. The resultant product was collected by filtration and dried to give 7.3 g (26% yield) of pure 1-(benzyloxycarbonyl)-3,3-dinitroazetidine. The melting point of the product was 77.5°-78°. Later runs with longer reaction times between the 1-tertiary-butyl-3,3-dinitroazetidine and benzyl chloroformate in refluxing methylene chloride afforded higher yields.
Workup
- customa white precipitate was formed
- temperatureto cool
- customwas separated by filtration
- washThe filter cake was washed with methylene chloride, air
- customdried
Sources & evidence
- ORD record
- ord-c477b0c9a08d4073a8215e6c5f219a49
- Source dataset
- uspto-grants-1995_03
- Patent number
- US05395945
Reaction notes
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