Hydrochloric Acid → 1,3-Benzenediamine, 2,4,6-trinitro-

HRID 1781925Notes

Reaction equation

HRID 1781925 reaction equation
[CH:1]1[C:6]([N+:7]([O-:9])=[O:8])=[C:5]([NH2:10])[C:4]([N+:11]([O-:13])=[O:12])=[CH:3][C:2]=1[N+:14]([O-:16])=[O:15].C(O[NH2:25])C1C=CC=CC=1.C[O-].[Na+].Cl>CS(C)=O>[CH:1]1[C:2]([N+:14]([O-:16])=[O:15])=[C:3]([NH2:25])[C:4]([N+:11]([O-:13])=[O:12])=[C:5]([NH2:10])[C:6]=1[N+:7]([O-:9])=[O:8]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 102712,4,6-TrinitroanilineHCID 102313O-BenzylhydroxylamineHCID 10942334Sodium Methoxide

Product 1

HCID 153961,3-Benzenediamine, 2,4,6-trinitro-Yield 87.4%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

DMSO (15 ml) is added with rapid stirring to a mixture of picramide (0.477 g, 2.09 mmol), O-benzylhydroxylamine (1.64 g, 10.3 mmol) and sodium methoxide (1.91 g, 35.4 mmol). The brown suspension is stirred at ambient temperature for 15 hr. The reaction mixture is poured into cold 0.12N aqueous HCl (200 ml). The resulting precipitate is collected, washed with water and dried to yield 0.444 g (87%) of DATB.

Workup

  1. customThe resulting precipitate is collected
  2. washwashed with water
  3. customdried

Sources & evidence

ORD record
ord-3c454c91ecb24bbd82b66c7cb9c203d6
Source dataset
uspto-grants-1997_05
Patent number
US05633406

Reaction notes

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