2,4,6-Trinitroaniline → 1,3-Benzenediamine, 2,4,6-trinitro-

HRID 1108874Notes

Reaction equation

HRID 1108874 reaction equation
C[O-].[Na+].[O-]CC.[Na+].CC(C)[O-].[Na+].CC(C)([O-])C.[Na+].[CH:19]1[C:24]([N+:25]([O-:27])=[O:26])=[C:23]([NH2:28])[C:22]([N+:29]([O-:31])=[O:30])=[CH:21][C:20]=1[N+:32]([O-:34])=[O:33].CC([N:38](C)C)=O>CN(C=O)C.CS(C)=O>[CH:19]1[C:20]([N+:32]([O-:34])=[O:33])=[C:21]([NH2:38])[C:22]([N+:29]([O-:31])=[O:30])=[C:23]([NH2:28])[C:24]=1[N+:25]([O-:27])=[O:26]

Participants

9

Reactant 6

HCID 102712,4,6-TrinitroanilineHCID 31374DimethylacetamideHCID 2723922Sodium ethoxideHCID 109204432-Propanol, sodium salt (1:1)HCID 10942334Sodium MethoxideHCID 23676156Sodium t-butoxide

Product 1

HCID 153961,3-Benzenediamine, 2,4,6-trinitro-

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 6228DimethylformamideSolvent

Procedure

Similarly, when Example 4(a) is repeated except that DMSO is replaced by a volumetrically equivalent amount of DMF or DMAC and sodium methoxide is replaced by a stoichiometrically equivalent amount of sodium ethoxide, sodium n-propoxide, sodium isopropoxide, or sodium tert-butoxide respectively, a mixture of picramide and DATB is produced. The DATB is purified by crystallization from DMF and DMSO.

Sources & evidence

ORD record
ord-4d34375d1c01437497c6271bc8789e27
Source dataset
uspto-grants-2000_05
Patent number
US06069277

Reaction notes

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