Acetic Acid → 8-Chlorotetrazolo[1,5-a]pyrazine

HRID 1045731Notes

Reaction equation

HRID 1045731 reaction equation
[Cl:1][C:2]1[C:7]([NH:8][NH2:9])=[N:6][CH:5]=[CH:4][N:3]=1.CC(O)=O.[N:14]([O-])=O.[Na+]>O>[Cl:1][C:2]1[C:7]2[N:6]([N:14]=[N:9][N:8]=2)[CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 3214302-Chloro-3-hydrazinopyrazineHCID 23668193Sodium Nitrite

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
10 °C

Procedure

A 2 L round bottom flask was charged with 2-chloro-3-hydrazinylpyrazine (440 g, 3.0 mol) and CH3COOH (500 mL). To the above was added dropwise a solution of NaNO2 (220 g, 3.2 mol) in water (200 mL) at 10° C. The resulting mixture was stirred at 10° C. for 1 h. Work-up: the resulting crystalline solid was collected by filtration, washed with EtOH (200 mL), and dried to afford 350 g (73%) of the product as a red solid.

Workup

  1. filtrationthe resulting crystalline solid was collected by filtration
  2. washwashed with EtOH (200 mL)
  3. customdried

Sources & evidence

ORD record
ord-dfd23c925f5248f59b31d3f18e0b1c5c
Source dataset
uspto-grants-2013_10
Patent number
US08569300B2

Reaction notes

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