Trimethylsilyl cyanide → 3,5-Diamino-2,4,6-trinitrobenzonitrile

HRID 344561Notes

Reaction equation

HRID 344561 reaction equation
F[C:2]1[C:3]([N+:16]([O-:18])=[O:17])=[C:4]([NH2:15])[C:5]([N+:12]([O-:14])=[O:13])=[C:6]([NH2:11])[C:7]=1[N+:8]([O-:10])=[O:9].[C:19]([Si](C)(C)C)#[N:20]>C[N+]([O-])=O>[C:19]([C:2]1[C:3]([N+:16]([O-:18])=[O:17])=[C:4]([NH2:15])[C:5]([N+:12]([O-:14])=[O:13])=[C:6]([NH2:11])[C:7]=1[N+:8]([O-:10])=[O:9])#[N:20]

Participants

4

Reactant 2

HCID 82115Trimethylsilyl cyanideHCID 52561041,3-Benzenediamine, 5-fluoro-2,4,6-trinitro-

Product 1

HCID 135723263,5-Diamino-2,4,6-trinitrobenzonitrileYield 82%

Reagents, catalysts & solvents 1

HCID 6375NitromethaneSolvent

Procedure

A solution of 5-fluoro-1,3-diamino-2,4,6-trinitrobenzene (F-DATB) (5.22 g, 20 mmol) and cyanotrimethylsilane (4.96 g, 50 mmol) in CH3NO2 (100 ml) was refluxed for two hours and then evaporated under vacuum to leave a solid residue. Recrystallization from acetonitrile (100 ml) gave 5-cyano-1,3-diamino-2,4,6-trinitrobenzene (4.4 g, 82%) as orange-brown crystals: mp 212°-217° C. dec. An additional recrystallization gave the analytical sample: mp 220°-221° C.; mass spectrum (CI, CH4) m/z 269 (M+1, 100).

Workup

  1. customevaporated under vacuum
  2. customto leave a solid residue
  3. customRecrystallization from acetonitrile (100 ml)

Sources & evidence

ORD record
ord-64737a66e4624a0c97fc3693ff1f3b05
Source dataset
uspto-grants-1991_10
Patent number
USH0000973

Reaction notes

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