Methanol → Pyrazine-2-carboxamidine hydrochloride

HRID 2112599Notes

Reaction equation

HRID 2112599 reaction equation
CO.[Na].[N:4]1[CH:9]=[CH:8][N:7]=[CH:6][C:5]=1[C:10]#[N:11].[Cl-:12].[NH4+:13]>C(OCC)C>[ClH:12].[N:4]1[CH:9]=[CH:8][N:7]=[CH:6][C:5]=1[C:10]([NH2:13])=[NH:11]

Participants

6

Reactant 4

HCID 887MethanolHCID 25517Ammonium ChlorideHCID 73172PyrazinecarbonitrileHCID 5360545Sodium

Product 1

HCID 470895Pyrazine-2-carboxamidine hydrochlorideYield 86.1%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To 20 mL of methyl alcohol is added sodium (109 mg, 4.74 mmol) with stirring. After disappearance of the solid, 2-pyrazinecarbonitrile (5.0 g, 47.6 mmol) is added. The mixture is stirred at room temperature for 6 h, and ammonium chloride (2.8 g, 52.3 mmol) is added. The mixture is then stirred at room temperature for 18 h. Diethyl ether (50 mL) is added to the reaction mixture, and the precipitates are collected by filtration. The solid was washed with diethyl ether (×2) and dried in vacuum oven to give 2-pyrazinecarboxamidine hydrochloride as a white solid (6.5 g). MS: m/z 123.1 (M+H).

Workup

  1. stirringThe mixture is stirred at room temperature for 6 h
  2. stirringThe mixture is then stirred at room temperature for 18 h
  3. filtrationthe precipitates are collected by filtration
  4. washThe solid was washed with diethyl ether (×2)
  5. customdried in vacuum oven

Sources & evidence

ORD record
ord-56db85a4d8f64bbbbd0cd981f289cc70
Source dataset
uspto-grants-2009_04
Patent number
US07524849B2

Reaction notes

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