Sodium → HCID 178507074, compound

HRID 989564Notes

Reaction equation

HRID 989564 reaction equation
Cl[C:2]1[N:3]=[N:4][C:5](Cl)=[N:6][N:7]=1.[Na].[NH2:10][C:11]1[NH:15][N:14]=[N:13][N:12]=1>C(#N)C>[NH:12]1[C:11]([NH:10][C:2]2[N:3]=[N:4][C:5]([NH:10][C:11]3[NH:15][N:14]=[N:13][N:12]=3)=[N:6][N:7]=2)=[N:15][N:14]=[N:13]1

Participants

5

Reactant 3

HCID 5360545SodiumHCID 136733773,6-Dichloro-1,2,4,5-tetrazineHCID 178509299HCID 178509299, compound

Product 1

HCID 178507074HCID 178507074, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 3,6-dichloro-1,2,4,5-tetrazine (1.51 g, 10 mmol) in acetonitrile (70 ml) was added the sodium salt of 5-amino-1H-tetrazole (2.14 g, 10 mmol). The mixture was refluxed for 24 hours then allowed to cool to room temperature. The suspension was centrifuged until the supernatant liquid was clear. The liquid was decanted and the brown solid washed successively with acetonitrile and water. With each wash the solid was separated from the solvent by centrifugation followed by decantation. The isolated crude yield was 1.5 g (60%), this material was recrystallized from DMSO/methanol yielding an orange brown powder mp 264° C. dec; 1H NMR (deuteriomethylsulfoxide) ∂ 12.5 (br s, 4H); 13C NMR (deuteriomethylsulfoxide) ∂ 151.74, 158.25; IR (KBr) 3421, 3000, 1615, 1436, 1127 cm−1. A gas pycnometer density of 1.76 g/cm3 was also determined and a drop height of 195 cm was measured (Type 12, HMX=24-27 cm).

Workup

  1. temperatureThe mixture was refluxed for 24 hours
  2. customThe liquid was decanted
  3. washthe brown solid washed successively with acetonitrile and water
  4. washWith each wash the solid
  5. customwas separated from the solvent by centrifugation
  6. customThe isolated crude yield was 1.5 g (60%), this material was recrystallized from DMSO/methanol yielding an orange brown powder mp 264° C. dec

Sources & evidence

ORD record
ord-5e34ff6765e84dc6a752eb3949034ad5
Source dataset
uspto-grants-2002_10
Patent number
US06458227B1

Reaction notes

Loading…