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

HRID 1108875Notes

Reaction equation

HRID 1108875 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-4a8d17d437b94b29a502cef522a295c9
Source dataset
uspto-grants-2000_05
Patent number
US06069277

Reaction notes

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