Bromoform → 2-Bromo-5,6-dichloro-3-nitropyrazine

HRID 1649360Notes

Reaction equation

HRID 1649360 reaction equation
C(ON=O)CC(C)C.[Cl:9][C:10]1[N:11]=[C:12]([N+:18]([O-:20])=[O:19])[C:13](N)=[N:14][C:15]=1[Cl:16].C(Br)(Br)[Br:22]>>[Br:22][C:13]1[C:12]([N+:18]([O-:20])=[O:19])=[N:11][C:10]([Cl:9])=[C:15]([Cl:16])[N:14]=1

Participants

4

Reactant 3

HCID 5558BromoformHCID 8053Isoamyl NitriteHCID 130629765,6-Dichloro-3-nitropyrazin-2-amine

Product 1

HCID 130629802-Bromo-5,6-dichloro-3-nitropyrazine

Procedure

To 4.8 g isoamylnitrite in 150 ml bromoform heated to 95°-100° is added portionwise 5.0 g 5,6-dichloro-3-nitro-pyrazinamine. The reaction mixture is heated at reflux for 18 hours. After cooling, the bromoform is removed in vacuo to give an oil which is chromatographed on silica gel. The initial component to elute is 5,6-dichloro-2-bromonitropyrazine, which is obtained (2.6 g) as a viscous oil.

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureat reflux for 18 hours
  3. temperatureAfter cooling
  4. customthe bromoform is removed in vacuo
  5. customto give an oil which
  6. customis chromatographed on silica gel
  7. washThe initial component to elute
  8. customwhich is obtained (2.6 g) as a viscous oil

Sources & evidence

ORD record
ord-d6c1fbabf9d14d2680ff4e9bb4e34afb
Source dataset
uspto-grants-1983_11
Patent number
US04416882

Reaction notes

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