Nitric Acid → HCID 21503291, compound
Reaction equation
CCCCCCCCC.[N+:10]([O-:15])([N+:12]([O-])=O)=[O:11].[C:16](=[O:19])([O-:18])[O-:17].[K+:20].[K+].[Cl:22][C:23]([Cl:45])([Cl:44])[C:24]([N:26]1[CH2:33][CH:32]([N:34]=[O:35])[CH2:31][CH:30]([C:36](=[O:41])[C:37]([Cl:40])([Cl:39])[Cl:38])[NH:29]N(N=O)[NH:27]1)=[O:25].[N+]([O-])(O)=[O:47]>>[C:16](=[O:17])([O-:19])[O-:18].[K+:20].[K+:20].[Cl:22][C:23]([Cl:45])([Cl:44])[C:24]([N:26]1[CH2:33][CH:32]([N+:34]([O-:47])=[O:35])[CH2:31][CH:30]([C:36](=[O:41])[C:37]([Cl:40])([Cl:39])[Cl:38])[NH:29][N:12]([N+:10]([O-:15])=[O:11])[NH:27]1)=[O:25]Participants
Procedure
A suspension of 0.80g of 1,5-di(trichloroacetyl)-1,3,5,7-tetraazabicyclo[3.3.1.]nonane in 5ml. of liquid dinitrogen tetroxide was stirred in a closed container for 20 hours. The reaction mixture was poured into ice water and the solution was neutralized with potassium carbonate to give a solid precipitate which when recrystallized from nitromethane melted at 234°-235°; yield, 0.41 g. (43%) of 1,5-di(trichloroacetyl)-3,7-dinitrosooctahydrotetrazocine. Upon further treatment of the above precipitate with 4 ml. of 99% nitric acid at room temperature with stirring for 12 minutes, followed by quenching in 250 ml. ice and neutralization with potassium carbonate to a pH of about 8, a yield of 89% of 1,5-di(trichloroacetyl)-3,7-dinitrooctahydrotetrazocine was obtained. The melting point of the product when recrystalized from hot nitromethane was 275°-278° C. and the NMR peak was delta 6.05 (in acetone -d6). The calculated elemental analysis is 19.34% carbon, 1.62% hydrogen and 16.91% nitrogen. The analysis of the product showed 19.22% carbon, 1.56% hydrogen and 16.82% nitrogen.
Workup
- customto give a solid precipitate which when
- customrecrystallized from nitromethane melted at 234°-235°
- customyield
- customby quenching in 250 ml
Sources & evidence
- ORD record
- ord-88904e99e0a54799beb610aa23f8df57
- Source dataset
- uspto-grants-1976_10
- Patent number
- US03987034
Reaction notes
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