Hydrazine → 5-Chloro-6-hydrazinyl-3-nitropyrazin-2-amine

HRID 1903825Notes

Reaction equation

HRID 1903825 reaction equation
[NH2:1][NH2:2].[Cl:3][C:4]1[N:5]=[C:6]([N+:12]([O-:14])=[O:13])[C:7]([NH2:11])=[N:8][C:9]=1Cl>C(O)C>[Cl:3][C:4]1[N:5]=[C:6]([N+:12]([O-:14])=[O:13])[C:7]([NH2:11])=[N:8][C:9]=1[NH:1][NH2:2]

Participants

4

Reactant 2

HCID 9321HydrazineHCID 130629765,6-Dichloro-3-nitropyrazin-2-amine

Product 1

HCID 130629835-Chloro-6-hydrazinyl-3-nitropyrazin-2-amineYield 88%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 300 ml of ethanol was added 7.4 g (0.22 mole) of a 95% hydrazine solution. This solution was cooled to 10° and with stirring 20.9 g (0.1 mole) of 5,6-dichloro-3-nitropyrazinamine (l) was added portionwise. A dark precipitate formed immediately and the suspension was stirred for 1 hour at room temperature. The mixture was filtered and the resulting solid washed with ethanol, water, ethyl acetate, ethanol and air dried to afford 18.0 g (88%) of the desired hydrazine as a brown solid, m.p. 220°; ms:m/e 205. This solid was treated with acetone to form the isopropylidene derivative, m.p. 245°-246° (dec.).

Workup

  1. temperatureThis solution was cooled to 10°
  2. additionwas added portionwise
  3. customA dark precipitate formed immediately
  4. filtrationThe mixture was filtered
  5. washthe resulting solid washed with ethanol, water, ethyl acetate, ethanol and air
  6. customdried

Sources & evidence

ORD record
ord-aa7e1ebf2c7d46ec951c507123966cdb
Source dataset
uspto-grants-1984_03
Patent number
US04438266

Reaction notes

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