Ammonium Chloride → 4-Methoxybenzamidine Hydrochloride

HRID 324772

Reaction equation

HRID 324772 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[CH:5][CH:4]=1.C[O-].[Na+].[Cl-:14].[NH4+:15]>CO>[ClH:14].[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([C:7]([NH2:15])=[NH:8])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 701294-MethoxybenzonitrileHCID 10942334Sodium Methoxide

Product 1

HCID 123262194-Methoxybenzamidine HydrochlorideYield 26.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4-methoxybenzonitrile (10.0 g) in methanol (75 ml) was added sodium methoxide (0.41 g) and the reaction was stirred at room temperature for 5 days. Ammonium chloride (4.6 g) was added and the reaction was stirred overnight. The reaction was filtered and the filtrate concentrated to an oil. After the addition of ether the off-white precipitate was collected and dried to yield the title compound (3.77 g). Electrospray MS m/z 151 [M+H]+.

Workup

  1. stirringthe reaction was stirred overnight
  2. filtrationThe reaction was filtered
  3. concentrationthe filtrate concentrated to an oil
  4. additionAfter the addition of ether the off-white precipitate
  5. customwas collected
  6. customdried

Sources & evidence

ORD record
ord-aa1cfbf27b25427b87f0bd5f227295ac
Source dataset
uspto-grants-2001_04
Patent number
US06218538B1

Linked notes

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