Sodium → HCID 178507074, compound

HRID 431180Notes

Reaction equation

HRID 431180 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(b,r s,4H); 13 C NMR (deuteriomethylsulfoxide) ∂ 151.74, 158.25; IR (KBr) 3421, 3000, 1615, 1436, 1127 cm−1.

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-4f91abb62ff44eaba6b96414fc3c6d58
Source dataset
uspto-grants-2003_12
Patent number
US06657059B2

Reaction notes

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