2-Chloro-3-hydrazinopyrazine → 8-Chlorotetrazolo[1,5-a]pyrazine

HRID 535706Notes

Reaction equation

HRID 535706 reaction equation
[Cl:1][C:2]1[C:7]([NH:8][NH2:9])=[N:6][CH:5]=[CH:4][N:3]=1.[N:10]([O-])=O.[Na+]>C(O)(=O)C.O>[Cl:1][C:2]1[C:7]2[N:6]([N:10]=[N:9][N:8]=2)[CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 2

HCID 3214302-Chloro-3-hydrazinopyrazineHCID 23668193Sodium Nitrite

Product 1

HCID 126931908-Chlorotetrazolo[1,5-a]pyrazineYield 75%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Conditions

Temperature
10 °C

Procedure

2-Chloro-3-hydrazinylpyrazine (440 g, 3.0 mol) was suspended in acetic acid (500 mL) and cooled to 10° C. A solution of sodium nitrite (220 g, 3.2 mol) in water (200 mL) at 10° C. was added. The resulting mixture was stirred at 10° C. for 1 h, during which time a crystalline solid precipitated. The precipitate was collected by filtration, washed with ethanol (200 mL) and dried to afford the desired product as a red solid (350 g, 73% yield).

Workup

  1. customprecipitated
  2. filtrationThe precipitate was collected by filtration
  3. washwashed with ethanol (200 mL)
  4. customdried

Sources & evidence

ORD record
ord-d2499dccf4284405bc4fac8ecb30e1db
Source dataset
uspto-grants-2014_10
Patent number
US08859550B2

Reaction notes

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