4-Chlorobenzonitrile → 4-Chlorobenzene-1-carboximidamide hydrochloride

HRID 324770

Reaction equation

HRID 324770 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.C[O-].[Na+].[Cl-].[NH4+:14]>CO>[ClH:1].[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]([NH2:14])=[NH:7])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 121634-ChlorobenzonitrileHCID 25517Ammonium ChlorideHCID 10942334Sodium Methoxide

Product 1

HCID 2034364-Chlorobenzene-1-carboximidamide hydrochlorideYield 104.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4-chlorobenzonitrile (5.0 g) in methanol (40 ml) was added sodium methoxide (0.20 g) and the reaction was stirred at room temperature for 3 days. Ammonium chloride (1.94 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 give the title compound (3.62 g). Electrospray MS m/z 155 [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-b654f5a2fedb4bb69a480af9c74c55cc
Source dataset
uspto-grants-2001_04
Patent number
US06218538B1

Linked notes

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