Water → HCID 15250323, compound

HRID 1655074Notes

Reaction equation

HRID 1655074 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].[NH2:19][C:20]([NH2:22])=[O:21].O>CN(C)C=O>[NH: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])[C:20]([NH2:22])=[O:21]

Participants

5

Reactant 3

HCID 962WaterHCID 1176UreaHCID 52561041,3-Benzenediamine, 5-fluoro-2,4,6-trinitro-

Product 1

HCID 15250323HCID 15250323, compoundYield 92.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 5-fluoro-1,3-diamino-2,4,6trinitrobenzene (1.57 g, 6 mmol) and urea (1.80 g, 30 mmol) in 30 ml of dry dimethylformamide (DMF) was heated for 1 hour at 90° C. A yellow precipitate formed after about 5 minutes. The mixture was cooled, poured into 150 ml of cold H2O and the solid filtered. Trituration of the solid with warm DMF-H2O (1:1, 100 ml), filtration and drying gave 5-ureido-1,3-diamino-2,4,6-trinitrobenzene (1.67 g, 92.3%): mp 350° C. dec; IR (KBr) 1730 cm-1 (C=O); mass spectrum (CI, CH4) m/z 259 (M+1-HNCO, 100).

Workup

  1. customA yellow precipitate formed after about 5 minutes
  2. temperatureThe mixture was cooled
  3. filtrationthe solid filtered
  4. filtrationTrituration of the solid with warm DMF-H2O (1:1, 100 ml), filtration
  5. customdrying

Sources & evidence

ORD record
ord-94102ccf8c304e50a135a9ae9a47446f
Source dataset
uspto-grants-1995_04
Patent number
US05410079

Reaction notes

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