Nitric Acid → Tnaz

HRID 1954461Notes

Reaction equation

HRID 1954461 reaction equation
C([N:5]1[CH2:8][C:7]([N+:12]([O-:14])=[O:13])([N+:9]([O-:11])=[O:10])[CH2:6]1)(C)(C)C.[N+:15](C1([N+]([O-])=O)CNC1)([O-:17])=[O:16].B(F)(F)F.CCOCC.C(OC(=O)C)(=O)C.[N+]([O-])(O)=O>>[CH2:6]1[N:5]([N+:15]([O-:17])=[O:16])[CH2:8][C:7]1([N+:9]([O-:11])=[O:10])[N+:12]([O-:14])=[O:13]

Participants

6

Reactant 5

HCID 944Nitric AcidHCID 7918Acetic AnhydrideHCID 8000Boron trifluoride etherateHCID 52317063,3-DinitroazetidineHCID 10954639Tert-butyl-3,3-dinitroazetidine

Product 1

HCID 9794126TnazYield 90%

Procedure

The upper reaction scheme is the conversion of the N-tertiarybutyl,3,3 dinitroazetidine to the N-acetyl, 3,3 dinitroazetidine. The reaction conditions are a catalytic amount of boron trifluoride etherate as the Lewis acid and acetic anhydride as the solvent-reactant. The temperature is 125 degrees C. As shown there was about a 90% yield. The compound is nitrated with 70% nitric acid and heated to give TNAZ.

Workup

  1. customThe upper reaction scheme
  2. customThe reaction conditions
  3. customis 125 degrees C
  4. temperatureheated

Sources & evidence

ORD record
ord-465b1afecccc489a9136522d4b31cf81
Source dataset
uspto-grants-2000_09
Patent number
US06121462

Reaction notes

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