p-Tolunitrile → 4-Methylbenzene-1-carboximidamide hydrochloride

HRID 324771

Reaction equation

HRID 324771 reaction equation
[C:1]1([CH3:9])[CH:6]=[CH:5][C:4]([C:7]#[N:8])=[CH:3][CH:2]=1.C[O-].[Na+].[Cl-:13].[NH4+:14]>CO>[ClH:13].[C:1]1([CH3:9])[CH:6]=[CH:5][C:4]([C:7]([NH2:14])=[NH:8])=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 7724p-TolunitrileHCID 25517Ammonium ChlorideHCID 10942334Sodium Methoxide

Product 1

HCID 1227534-Methylbenzene-1-carboximidamide hydrochlorideYield 31%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of p-tolunitrile (10.0 g) in methanol (85 mlb) was added sodium methoxide (0.46 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 give the title compound (4.52 g). Electrospray MS m/z 135 [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-5aa06194480444fd8bcc6bf2fb801662
Source dataset
uspto-grants-2001_04
Patent number
US06218538B1

Linked notes

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